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Potassium Hydroxide → 2-benzylsulfanylmethyl-3-(3-cyano-benzylsulfanyl)-N-cyanomethyl-propionamide

HRID 1830168
Notes
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Reaction equation

HRID 1830168 reaction equation
[CH2:1]([S:8][CH2:9][CH:10]([C:16](=[O:21])[NH:17][CH2:18][C:19]#[N:20])[CH2:11][S:12][C:13](=O)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:24]([C:26]1[CH:27]=C([CH:31]=[CH:32][CH:33]=1)CBr)#[N:25]>CN(C)C=O.O>[CH2:1]([S:8][CH2:9][CH:10]([CH2:11][S:12][CH2:13][C:14]1[CH:31]=[CH:32][CH:33]=[C:26]([C:24]#[N:25])[CH:27]=1)[C:16]([NH:17][CH2:18][C:19]#[N:20])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 86611134thioacetic acid S-[3-benzylsulfanyl-2-(cyanomethyl-carbamoyl)-propyl]ester

Product 1

HCID 220539752-benzylsulfanylmethyl-3-(3-cyano-benzylsulfanyl)-N-cyanomethyl-propionamideYield 104.8%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent2×

Procedure

A solution of thioacetic acid S-[3-benzylsulfanyl-2-(cyanomethyl-carbamoyl)propyl] ester (0.105 g) in dimethylformamide (1 mL) and water (0.8 mL) was cooled on ice and treated with 1 N aqueous potassium hydroxide (0.65 mL). 3-Cyanobenzylbromide (0.129 g) in dimethylformamide (0.8 mL) was added. The reaction mixture was allowed to warm to room temperature while stirring overnight. The reaction mixture was then poured into ice water and extracted with ethyl acetate (50 mL) and washed with water and saturated aqueous sodium chloride. The solution was dried over magnesium sulfate and evaporated to give 2-benzylsulfanylmethyl-3-(3-cyano-benzylsulfanyl)-N-cyanomethyl-propionamide (0.135 g).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washwashed with water and saturated aqueous sodium chloride
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1219ba2fc5f44b9d83441c0240370ecf
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07064123B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes