Imidazole → HCID 153274962, compound

HRID 2304698Notes

Reaction equation

HRID 2304698 reaction equation
F[C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9](=[NH:24])[NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)=[O:7])=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:31]1([C:15]2[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:9](=[NH:24])[NH:8][C:6](=[O:7])[C:5]3[CH:25]=[CH:26][C:2]([N:31]4[CH:35]=[CH:34][N:33]=[CH:32]4)=[C:3]([C:27]([F:30])([F:28])[F:29])[CH:4]=3)=[O:23])=[CH:13][C:14]=2[C:19]([F:20])([F:21])[F:22])[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 172811235HCID 172811235, compound

Product 1

HCID 153274962HCID 153274962, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.25 g of bis(4-fluoro-3-trifluoromethylbenzoyl)guanidine, 0.16 g of imidazole and 0.16 g of potassium carbonate are heated for 16 h in 5 ml of DMF, and after that the solvent is evaporated. Separation of the crude product by column chromatography yielded 0.12 g of bis[4-(1-imi-dazolyl)-3-trifluoromethylbenzoyl]guanidine as a colorless solid, mp 130° C., decomp., Rf (CH2Cl2/MeOH 9:1)=0.4 MS (ES): 536 (M+1) and 0.07 g of N-[4-(1-imidazolyl)-3-trifluoromethylbenzoyl]-N′-(4-fluoro-3-trifluoromethylbenzoyl)guanidine as an oil. Treatment with HClg/ether yielded 0.06 g of N-[4-(1-imidazolyl)-3-trifluoromethylbenzoyl]-N′-(4-fluoro-3-trifluoromethylbenzoyl)guanidine hydrochloride as a colorless solid, mp 217-218, decomp., Rf (CH2Cl2/MeOH 9:1)=0.53; MS (ES): 488 (M+1)

Workup

  1. customafter that the solvent is evaporated
  2. customSeparation of the crude product by column chromatography

Sources & evidence

ORD record
ord-1afdd321dfdd4560bb5dcdf1892fc397
Source dataset
uspto-grants-2002_08
Patent number
US06436999B1

Reaction notes

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