Acetic Acid → 3-((2-amino-4-chlorophenyl)thio)-N,N-dimethylpropanamide

HRID 70363

Reaction equation

HRID 70363 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].[CH3:10][N:11]([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14].CC(O)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:14][CH2:13][C:12]([N:11]([CH3:16])[CH3:10])=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120002-Amino-4-chlorobenzenethiolHCID 17587N,N-Dimethylacrylamide

Product 1

HCID 609618703-((2-amino-4-chlorophenyl)thio)-N,N-dimethylpropanamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 2-amino-4-chlorobenzenethiol (824 mg, 5.126 mmol), N,N-dimethylacrylamide (512 mg, 5.162 mmol), and HOAc (1 ml) in CH2Cl2 (10 ml) was stirred at room temperature for 4 days. The solvent was removed and the residue was loaded on silica column and purified to yield a white solid (1.08 g, 83%).

Workup

  1. customThe solvent was removed
  2. custompurified

Sources & evidence

ORD record
ord-d56a93cafd944ebe8d2c4ac166229472
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Linked notes

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