Water → Methyl 3-phenyl-5-(phenylcarbamoyl)thiophene-2-carboxylate

HRID 1186718Notes

Reaction equation

HRID 1186718 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[C:19]1([NH2:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O>CN(C=O)C>[C:13]1([C:6]2[CH:7]=[C:8]([C:10](=[O:12])[NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:9][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 581210855-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acid

Product 1

HCID 58121116Methyl 3-phenyl-5-(phenylcarbamoyl)thiophene-2-carboxylateYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 174 (0.334 g, 1.273 mmol) in 6 mL DMF was added PhNH2 (0.128 ml, 1.401 mmol), followed by BOP (0.620 g, 1.401 mmol) and TEA (0.355 ml, 2.55 mmol). The mixture was stirred for 1 h at room temperature and then poured into water. The product was extracted with ethyl acetate twice and the combined organic phases were washed with water and brine. The solution was dried over sodium sulfate, filtered and evaporated in vacuo. The crude residue was purified by ISCO (24 g column, 0%-100% ethyl acetate in hexanes) to yield compound 175 (285 mg, 66%) a off-white solid.

Workup

  1. extractionThe product was extracted with ethyl acetate twice
  2. washthe combined organic phases were washed with water and brine
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude residue was purified by ISCO (24 g column, 0%-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c8b0fa339bc646a9b8691bb08ec1442e
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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