Dimethylformamide → 5-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

HRID 605313Notes

Reaction equation

HRID 605313 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=2[N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[Br:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35]>ClCCl.C(OCC)(=O)C.O.N1C=CC=CC=1>[Br:31][C:32]1[CH:33]=[C:34]([NH:35][C:14]([C:12]2[S:13][C:9]([S:8][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[O:16])[CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 115623-BromoanilineHCID 65578Oxalyl chlorideHCID 670406395-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid

Product 1

HCID 670409995-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 351C was dissolved in dichloromethane followed by the addition of a solution of oxalyl chloride and a catalytic amount of dimethylformamide. The solution was stirred at room temperature for 3 hours followed by the addition of 3-bromoaniline and pyridine. The resultant solution was stirred at room temperature for 20 hours followed by the addition of water and extraction of the solution with ethyl acetate, the organic extracts dried and concentrated under vacuum to provide the crude product, which was purified by silica gel chromatograpy to provide the title product.

Workup

  1. customthe organic extracts dried
  2. concentrationconcentrated under vacuum
  3. customto provide the crude product, which
  4. customwas purified by silica gel chromatograpy

Sources & evidence

ORD record
ord-ab90165e53c14013b1b83a758ed72568
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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