Hydrochloric Acid → 1-Methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:13])[CH3:12].[CH3:15][O:16][C:17]([N:19]=[C:20]=[S:21])=[O:18].Cl>C(#N)C.C(OCC)C>[CH3:15][O:16][C:17]([NH:19][C:20]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][N:11]([CH3:12])[CH3:13])=[S:21])=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of N-(2-aminophenyl)-2-dimethylaminoacetamide (4.8 g) in dry acetonitrile (20 ml) was stirred vigorously during the dropwise addition of methoxycarbonyl isothiocyanate (3.5 g), the temperature being maintained between 15° C. and 20° C. by external cooling, and afterwards for a further 5 minutes. The mixture was then diluted with diethyl ether (500 ml) and treated with an excess of a saturated solution of hydrogen chloride in diethyl ether. The precipitate was filtered off, dissolved in the minimum quantity of water, and treated with an excess of a 2N aqueous solution of sodium hydroxide. The precipitate was filtered off and recrystallised twice from benzene to give 1-methoxycarbonyl-3-(2-dimethylaminoacetamidophenyl)thiourea (3.5 g), m.p. 130°-131° C. (with decomposition).
Workup
- temperaturethe temperature being maintained between 15° C. and 20° C. by external cooling
- filtrationThe precipitate was filtered off
- dissolutiondissolved in the minimum quantity of water
- additiontreated with an excess of a 2N aqueous solution of sodium hydroxide
- filtrationThe precipitate was filtered off
- customrecrystallised twice from benzene
Sources & evidence
- ORD record
- ord-df85cab9cb044e3795344c26553d0865
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04005217
Reaction notes
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