Formic Acid → 6-Benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)benzimidazole

HRID 1699623Notes

Reaction equation

HRID 1699623 reaction equation
[C:1]1([S:7]([NH:10][C:11](=[O:33])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)[CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:34](O)=O>>[C:1]1([S:7]([NH:10][C:11]([C:12]2[CH:17]=[CH:16][C:15]3[N:18]=[CH:34][N:19]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:23][CH:22]=4)[C:14]=3[CH:13]=2)=[O:33])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 53635937N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide

Product 1

HCID 537801916-Benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)benzimidazole

Conditions

Temperature
90 °C

Procedure

A mixture of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino) benzamide (0.400 g) and formic acid (2 ml) is stirred for three hours at 90° C. The reaction solution is concentrated. The crystals which precipitated by adding methanol are separated through filtration, dried and thus, 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)benzimidazole (0.243 g) is obtained. 1H-NMR (DMSO-d6, δ): 5.60 (2H, s), 7.35 (1H, t, J=7.2 Hz), 7.39 (2H, d, J=8.2 Hz), 7.44 (2H, t, J=7.6 Hz), 7.61-7.77 (9H, m), 8.00 (2H, d, J=7.7 Hz), 8.26 (1H, s), 8.66 (1H, s), 12.5 (1H, s).

Workup

  1. concentrationThe reaction solution is concentrated
  2. customThe crystals which precipitated
  3. additionby adding methanol
  4. customare separated through filtration
  5. customdried

Sources & evidence

ORD record
ord-d67915b248cc4bfdaf1028aa749f6737
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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