Triethylamine → HCID 22603416, compound

HRID 2307913Notes

Reaction equation

HRID 2307913 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([OH:17])=[O:16])=[C:7]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[Cl:27]N1C(=O)CCC1=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([Cl:27])(=[O:17])=[O:16])=[C:7]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 22603439HCID 22603439, compound

Product 1

HCID 22603416HCID 22603416, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,4-Dichlorobenzyl)-2-ethoxycarbonylindole-3-sulphinic acid (0.48 g), N-chlorosuccinimide (0.16 g) and triethylamine (0.16 ml) were stirred in dichloromethane for 4 hours. The reaction was then concentrated in vacuo and the residue purified by chromatography using iso-hexane:10% ethyl acetate as eluent to give the product as a white crystalline solid (0.27 g, 52%); NMR d (CD3SOCD3) 1.43 (t, 3H), 4.48 (q, 2H), 5.53 (s, 2H), 6.98 (m, 1H), 7.30-7.50 (m, 5H), 8.22 (m, 1H); M/z (−) 444 (M−H+), 426, 410.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-1d55ea17f9934e0c93a106901ec0846c
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

Loading…