Urea, 1-phenyl-2-thio

Phenyl Thio UREA (Phenyl thio carbamide) CS.NHj.NHC,H,. Solubility in Water. 

Benzene- sulphon- amlde /)-Tolu- enesul- phon- amlde Benzal Derivative Plcrate 3-Nltro- phthal- Imlde 2 4- Dinitro- phenyl Derivative Formyl Derivative Phenyl thio- urea... 

This reaction does not take place with aromatic amines. With aniline, for example, there is obtained instead a compound known as di-phenyl thio-urea, hydrogen sulphide being eliminated. On heating the diphenyl thio-urea with acids one molecule of aniline is lost and phenyl iso-thio-cyanate is obtained (p. 421). 

Di-phenyl thio-urea is a di-phenyl derivative of thio-urea, the sulphur analogue of urea. 

Solubility of Phenyl Thio Urea in Aqueous Salt Solutions at ao . 

Solubility op Phenyl Thio Urea in Aqueous Solutions op Propyl and op Ethyl Alcohol at 25°. 

Figure 6.3 Stereoselective, chiral thiourea derivatives of achiral benchmark thiourea organocatalyst N,N -bis [3,5-(trifluoromethyl)phenyl]thiourea 9 stereoselective hydrogen-bonding thiourea organocatalysts incorporating the privileged 3,5-bis(trifluoromethylphenyl)thiourea moiety. The (thio)urea catalyst structure is the leitmotif for the chapter organization.

Ricci and co-workers introduced a new class of amino- alcohol- based thiourea derivatives, which were easily accessible in a one-step coupling reaction in nearly quanitative yield from the commercially available chiral amino alcohols and 3,5-bis(trifluoromethyl)phenyl isothiocyanate or isocyanate, respectively (Figure 6.45) [307]. The screening of (thio)urea derivatives 137-140 in the enantioselective Friedel-Crafts reaction of indole with trans-P-nitrostyrene at 20 °C in toluene demonstrated (lR,2S)-cis-l-amino-2-indanol-derived thiourea 139 to be the most active catalyst regarding conversion (95% conv./60h) as well as stereoinduction (35% ee), while the canditates 137, 138, and the urea derivative 140 displayed a lower accelerating effect and poorer asymmetric induction (Figure 6.45). The uncatalyzed reference reaction performed under otherwise identical conditions showed 17% conversion in 65 h reaction time. 

A screening of (R)-bis-N-tosyl-BlNAM 151 and axially chiral (thio)urea derivatives 152-162 (10mol% loading 0.36 M catalyst concentration incorporating the N-aryl(alkyl) structural motif was performed at various reaction temperatures in di-chloroform using the asymmetric FC addition of N-methylindole to trans-Ji-nitrostyrene as model reachon (product 1 Scheme 6.158). The structure of bis(3,5-bistrifluoromethyl) phenyl functionalized binaphthyl bisthiourea 158 was identified... 

M. Shi and Y.-L. Shi reported the synthesis and application of new bifunctional axially chiral (thio) urea-phosphine organocatalysts in the asymmetric aza-Morita-Baylis-Hillman (MBH) reaction [176, 177] of N-sulfonated imines with methyl vinyl ketone (MVK), phenyl vinyl ketone (PVK), ethyl vinyl ketone (EVK) or acrolein [316]. The design of the catalyst structure is based on axially chiral BINOL-derived phosphines [317, 318] that have already been successfully utilized as bifunctional catalysts in asymmetric aza-MBH reactions. The formal replacement of the hydrogen-bonding phenol group with a (thio)urea functionality led to catalysts 166-168 (Figure 6.51). 

Mesoionic pyrido[2,l- >][1,3]oxazines (54) afforded 4-oxo-4//-pyrido[l,2-a]pyrimidin-l-iumolates (55) and 4//-quinolizin-4-one (56) with phenyl iso(thio)cyanates [78LA1655 79CB1585 82ZN(B)222] and dimethyl acetylenedicarboxylate (79CB1585), respectively. Reaction of 2-cyano-3-methyl-lH,6//-pyridol[l,2-a][3,l]benzoxazine-l,6-dione with ammonium acetate and hydroxylamine, hydrazines, primary aliphatic or aromatic amines, and (thio)ureas gave 5-unsubstituted and 5-substituted 2-cyano-3-methyl-l//,6H-pyrido[l,2-a]quinazoline-l,6-diones (93CCC1953). 

Solvent-free three-component Biginelli reactions of 2-phenyl-l,3-oxazol-5-one, D-xylose/D-glucose and (thio)ureas 136 in the presence of Ce2(S04)3 salt (10%) under microwave irradiation produced perhydropyrido[l,2-c] pyrimidines 137 and 138 with 94% trans diastereoselectivity (Scheme 3). In the absence of Ce3+ salt no reaction occurred, and without microwave irradiation using conventional heating at 90 °C yields were significantly lower (39-51%) even for longer reaction times (3-5 h). If shorter reaction periods (4-7 min) was applied addition products 139 could be isolated, which then were converted to pyrido[l,2-c]pyrimidines 137 (X = O, R = H) and 138 (X = S, R = Ph) (07SL1905). 

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