1-Bromohexane → Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate

HRID 1164122Notes

Reaction equation

HRID 1164122 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[CH3:22])[C:10]=1[O:23][CH3:24])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>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[CH3:22])[C:10]=1[O:23][CH3:24])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 20513407Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetate

Product 1

HCID 20513448Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetate (4 g) in dimethylformamide (5 ml) was added dropwise to a solution of sodium hydride (purity 65%, 450 mg) in dimethylformamide (20 ml) in 10 minutes at temperature below 10° C. with stirring. After stirring the mixture at the same temperature for 10 minutes, n-hexyl bromide (3.85 g) was added to the mixture and stirred at 50° C. for an hour. After evaporation, water was added to the residue, and the mixture was extracted with diethyl ether. The extract was washed with water, dried and evaporated under reduced pressure to give oily ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate (5 g).

Workup

  1. stirringAfter stirring the mixture at the same temperature for 10 minutes
  2. stirringstirred at 50° C. for an hour
  3. customAfter evaporation, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9c484b65327e4997b896893ba695a6f2
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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