Reaction equation
C(N(CC)C(C)C)(C)C.Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=1.Cl.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][NH2:33]>O1CCCC1>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][NH:33][C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
At room temperature, 16.2 mL of N,N-diisopropylethylamine was added to tetrahydrofuran (300 mL) solution of 9.4 g of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate and 8.3 g of 2-chlorophenylhydrazine hydrochloride, and heated under reflux for 18 hours. The solvent was concentrated under reduced pressure, water was added to this, and extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain crude ethyl 4-[2-(2-chlorophenyl)hydrazino]-2-(methylthio)pyrimidine-5-carboxylate as a yellow oily substance.
Workup
- temperatureheated
- temperatureunder reflux for 18 hours
- concentrationThe solvent was concentrated under reduced pressure, water
- additionwas added to this, and
- extractionextracted with ethyl acetate
- washthe ethyl acetate layer was washed with saturated saline water
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated away under reduced pressure
Sources & evidence
- ORD record
- ord-48d5b8a2b45f43f19f7c8741247eb5ef
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935708B2
Linked notes
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