Water → HCID 20513408, compound

HRID 1164085Notes

Reaction equation

HRID 1164085 reaction equation
[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:10]=1[O:23][CH3:24])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[CH3:27]I.O>CN(C)C=O>[C:1]([C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:10]=1[O:23][CH3:24])([CH3:27])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20513507HCID 20513507, compound

Product 1

HCID 20513408HCID 20513408, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 2-cyano-2-[2-methoxy-3-(2-chlorophenylthio)phenyl]acetate (3.2 g) in dimethylformamide (10 ml) was added dropwise to a mixture of sodium hydride (65%, 330 mg) and dimethylformamide (20 ml) in 10 minutes at temperature below 10° C. After stirring the mixture at the same temperature for 20 minutes, methyl iodide (2.5 g) was added to the mixture. The mixture was stirred at the same temperature for 15 minutes and then at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water, dried and then evaporated under reduced pressure to give oily ethyl 2-cyano-2-[2-methoxy-3-(2-chlorophenylthio)phenyl]propionate (3.4 g).

Workup

  1. stirringThe mixture was stirred at the same temperature for 15 minutes
  2. waitat room temperature for 20 minutes
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5fccfbd8b994493eb224174cbc268624
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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