Water → Methyl 5-[[[1-methyl-2-(phenylmethylene)hydrazino](methylthio)methylene]amino]-5-oxopentanoate
Reaction equation
Cl[C:2]([CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:3].[CH3:11][N:12]([C:21]([S:23][CH3:24])=[NH:22])[N:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>ClCCl>[CH3:11][N:12]([C:21](=[N:22][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[S:23][CH3:24])[N:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Methyl 4-(chloroformyl)butyrate (31.2 g) was added dropwise during 1 h at 20° to a stirred solution of methyl 1-methyl-2-(phenylmethylene)hydrazine carboximidothioate (3.60 g) and triethylamine (20.0 g) in dichloromethane (100 ml). The pale yellow suspension was stirred at 20° C. for 16 h. A further portion of methyl 4-(chloroformyl)butyrate (6.2 g) and triethylamine (4.0 g) was added and stirring continued for a further 1 h. Water (100 ml) was added, the organic layer separated and washed successively with saturated aqueous sodium bicarbonate and water, dried, and evaporated to give a brown solid (53.6 g). This solid was recrystallised from ether to give the title compound (30.9 g) as a pale yellow solid m.p. 69°-70°.
Workup
- stirringstirring
- waitcontinued for a further 1 h
- customthe organic layer separated
- washwashed successively with saturated aqueous sodium bicarbonate and water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-4242df0f2a5b4d3ab656f9101330b731
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04476126
Reaction notes
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