Benzenesulfonamide → HCID 19806374, compound

HRID 1681375Notes

Reaction equation

HRID 1681375 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:8]2[CH:20]=[CH:21][CH:22]=[CH:23][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[C:24]1([S:30]([NH2:33])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH:33][S:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:32])=[O:31])=[O:17])=[CH:13][CH:12]=2)[C:8]2[CH:20]=[CH:21][CH:22]=[CH:23][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 7370BenzenesulfonamideHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 149872984-[(2-Butyl-1H-benzimidazol-1-yl)methyl]benzoic acid

Product 1

HCID 19806374HCID 19806374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[(2-Butyl-1H-benzimidazol-1-yl)methyl]benzoic acid (150 mg) was added to a solution of benzenesulphonamide (79 mg), dimethylaminopyridine (60 mg) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (91 mg) in dry dichloromethane (5 ml). The mixture was stirred overnight and then diluted with dichloromethane (20 ml). The solution was washed successively with 1M hydrochloric acid (20 ml), water (20 ml) and saturated brine (20 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue triturated with ether to give 4-[(2-butyl-1H-benzimidazol-1-yl)methyl]-N-phenylsulphonylbenzamide as a white solid, m.p. 241°-242° C.; NMR (d6 -DMSO): 0.9(t,3H), 1.35(m,2H), 1.7(m,2H), 2.85(t,2H), 5.6(s,2H), 7.2(m,3H), 7.4(m,1H), 7.6(m,4H). 7.8(d,2H), 8.0(d,2H); mass spectrum (-ve FAB, DMSO/m-nitrobenzyl alcohol): 446(M-H)- ; microanalysis found: C,66.7; H,5.6; N,9.1; C25H25N3O3S requires: C,67.1; H,5.6; N,9.4%.

Workup

  1. washThe solution was washed successively with 1M hydrochloric acid (20 ml), water (20 ml) and saturated brine (20 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by evaporation
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-624cd19604e54f69ac14e6c254d6e18e
Source dataset
uspto-grants-1992_12
Patent number
US05171748

Reaction notes

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