Sulfuryl chloride → HCID 14535763, compound

Reaction equation

[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[C:6]([NH:11][C:12](=[O:17])[CH2:13][C:14]([CH3:16])=O)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH2:19][C:20]([NH2:22])=[S:21].S(Cl)(Cl)(=O)=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[C:6]([NH:11][C:12]([C:13]3[S:21][C:20]([NH2:22])=[N:19][C:14]=3[CH3:16])=[O:17])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

Procedure

1.00 g (4.08 mmol) of N-(1,1-dimethyl-4-indanyl)acetoacetamide and 0.62 g (8.16 mmol) of thiourea were dissolved in 10 ml of benzene and to this solution was added dropwise a solution of 0.55 g (4.08 mmol) of sulfuryl chloride in 5 ml of benzene at room temperature. After reacting for 2 hours at this temperature, the reaction mixture was refluxed for 1 hour, and left overnight. Then, the resulting solution was concentrated and dissolved in hot water and thereafter neutralyzed with 28% aqueous ammonia to give a precipitate. This precipitate was filtered, washed with water and dried to obtain 1.00 g of N-(1,1-dimethyl-4-indanyl)-2-amino-4-methylthiazole-5-carboxamide (yield 81%).