Chloroform → HCID 15114494, compound

HRID 1757281Notes

Reaction equation

HRID 1757281 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3].[C:25]1([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.C(Cl)(Cl)Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:34][S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:33])=[O:32])=[O:21])=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15114492HCID 15114492, compound

Product 1

HCID 15114494HCID 15114494, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-[(2-Propylquinolin-4-yloxy)methyl]benzoic acid (240 mg) was added to a mixture of benzene sulphonamide (120 mg), 4-dimethylaminopyridine (90 mg) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (150 mg) in dichloromethane (20 ml) and the mixture stirred overnight. Chloroform (20 ml) was added the mixture was washed successively with 1M citric acid solution (10 ml), water (2×10 ml), saturated sodium chloride solution (5 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue triturated with methanol to give 4-[(2-propylquinolin-4-yloxy)methyl]-N-phenylsulphonylbenzamide as a white powder (160 mg), m.p. 140° C. (dec.); NMR (d6 -DMSO): 0.95(t,3H), 1.79(m,2H), 2.88(t,2H), 5.5(s,2H), 7.14(s,1H), 7.5-7.7(m,6H), 7.78(dt,1H), 7.87-8.02(m,5H), 8.18(dd,1H); mass spectrum (-ve FAB, DMSO/Gly): 495 (M-H)- ; microanalysis found: C,66.1; H,5.4; N,5.8%; C26H24N2O4S.0.5H 2 O requires: C,66.5; H,5.3; N,6.0%.

Workup

  1. washwas washed successively with 1M citric acid solution (10 ml), water (2×10 ml), saturated sodium chloride solution (5 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by evaporation
  4. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-70546ece2db143ba8534193770b0e411
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

Loading…