1,1'-Carbonyldiimidazole → 5-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amide

HRID 1673154Notes

Reaction equation

HRID 1673154 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:26][C:27]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30]>N1C=CC=CC=1.CN(C=O)C>[NH2:26][C:27]1[C:28]([C:29](=[O:30])[NH2:31])=[CH:32][CH:33]=[CH:34][C:35]=1[NH:36][C:9]([C:7]1[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 37427275-Acetylthiophene-2-carboxylic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 673537955-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amideYield 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-acetylthiophene-2-carboxylic acid (1.80 g, 10.55 mmol) in pyridine (12 mL) and N,N′-dimethylformamide (12 mL) was treated with 1,1′-carbonyldiimidazole (1.88 g, 11.60 mmol) at 45° C. for 4 hours. 2,3-Diaminobenzamide dihydrochloride (2.36 g, 10.55 mmol) was added and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the residue stirred in ethyl acetate and water, filtered, and the yellow solid washed with water and ethyl acetate and dried to give the title compound (2.91 g, 91%). MS(APCI): 304 (M+1)+.

Workup

  1. concentrationThe mixture was concentrated
  2. stirringthe residue stirred in ethyl acetate
  3. filtrationwater, filtered
  4. washthe yellow solid washed with water and ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-3da9a8fa6d0c40068b21ddca5cfe52b9
Source dataset
uspto-grants-2011_08
Patent number
US07999117B2

Reaction notes

Loading…