Methyl-1- 1-naphthyl -2-thiourea

This general reaction can be used for preparing other un-symmetrical thioureas when the desired cyanamides can be obtained. The submitter has also prepared l-methyl-l-(l-naph-thyl)-2-selenourea, m.p. 174-175° with decomposition, and l-ethyl-l-(l-naphthyl)-2-selenourea, m.p. 168-170° with decomposition, by substitution of hydrogen selenide for hydrogen sulfide. 

The thiourea can be further purified by recrystallization from ethanol. The recrystallized product melts at 170-171°. 

MUCOBROMIC ACID (Acrylic acid, a,p-dibromo-p-f ormyl-) 

Submitted by C. F. H. Allen and F. W. Spangler. Checked by R. L. Shriner and Nicholas J. Kartinos. 

250 ml. of boiling water with the addition of 2 g. of Darco. The hot solution is filtered, and the filtrate is thoroughly chilled in an ice bath. After filtration and drying there is obtained 148-155 g. (64-67%) of white crystals melting at 123-124° (cor.). 

---

Magnesium, 12, 48 Malononitrile, 10, 66 Malonylurea, see Barbituric acid Mercuration, 12, 46, 54 Mercuric chloride, 12, 54 Mercuric oxide, 12, 44 Mercury di-/3-naphthyl, 12, 46 Mesaconic acid, 11, 74 Mcsitylene, 11, 24, 67 Methylamine, 12, 38 Methylamine hydrochloride, 10, 112 Methyl -amyI ketone, 10, 60 M ethylation of thiourea, 12, 52 Methyl benzoate, 10, 51 Methyl chloride, 10, 32, 36 Methylene bromide, 10, 112... 

The thiazoline was obtained in the best yields and with the lightest color from freshly prepared l-methyl-l-(l-naphthyl)-2-thiourea. The air-dried thiourea loses hydrogen sulfide and ammonia after several days storage. 

Benzoin, tetraphenylethanediol, hydrazobenzene and 1,2-diphenyl-1,2-ethanedione bishydrazone are oxidized by methyl bis(l-naphthyl)bismuthi-nate to benzil, benzophenone, azobenzene and diphenylacetylene, respectively [88CL2021] (Section 5.2.4). Amides, thioamides, ureas and thioureas are A-acylated in good yield with acetic acid in the presence of the bismuthi-nate at room temperature [90CL1651] (Scheme 3.11). 

---