Dimethylformamide → n-[3-(2,3-Dimethyl-3h-imidazol4-yl)-phenyl]-5-phenyl-thiophene-2-carboxamide

HRID 1835453Notes

Reaction equation

HRID 1835453 reaction equation
[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:26][N:27]1[C:31]([C:32]2[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=2)[NH2:35])=[CH:30][N:29]=[C:28]1[CH3:39]>ClCCl.N1C=CC=CC=1>[CH3:39][C:28]1[N:27]([CH3:26])[C:31]([C:32]2[CH:33]=[C:34]([NH:35][C:12]([C:10]3[S:11][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][CH:9]=3)=[O:14])[CH:36]=[CH:37][CH:38]=2)=[CH:30][N:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7364945-Phenyl-2-Thiophenecarboxylic AcidHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Product 1

HCID 23503666n-[3-(2,3-Dimethyl-3h-imidazol4-yl)-phenyl]-5-phenyl-thiophene-2-carboxamideYield 83.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a suspension of 5-phenylthiophene-2-carboxylic acid (102 mg) and oxalyl chloride (0.2 ml) in dichloromethane (2 ml) was added N,N-dimethylformamide (0.01 ml), and the mixture was stirred for an hour. The resultant solution was evaporated under reduced pressure to give a crude acid chloride. To a suspension of 3-(1,2-dimethylimidazol-5-yl)aniline (94 mg) and pyridine (0.12 ml) in dichloromethane (2 ml) was dropwise added a solution of the acid chloride obtained above in dichloromethane (2 ml) followed by stirring for 12 hours. The mixture was diluted with dichloromethane and washed with an aqueous solution of sodium hydrogen carbonate and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-[3-(2,3-dimethyl-3H-imidazol4-yl)-phenyl]-5-phenyl-thiophene-2-carboxamide (155 mg, 82.9%).

Workup

  1. customThe resultant solution was evaporated under reduced pressure
  2. customto give a crude acid chloride
  3. stirringby stirring for 12 hours
  4. washwashed with an aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialThe separated organic layer was dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography
  8. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-6f9b9c6be8974c57a3ef541950c34616
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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