Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 178513458, compound

HRID 731546Notes

Reaction equation

HRID 731546 reaction equation
[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[NH:24])[NH2:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][C:42]=1[N+:51]([O-:53])=[O:52]>ClCCl>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([NH:24][C:22]([C:19]2[CH:20]=[CH:21][C:16]([N:13]3[CH2:14][CH2:15][N:10]([CH2:9][CH:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:11][CH2:12]3)=[CH:17][CH:18]=2)=[NH:23])(=[O:49])=[O:48])=[CH:43][C:42]=1[N+:51]([O-:53])=[O:52]

Participants

5

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 81531DiisopropylethylamineHCID 591866074-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzenecarboximidamide

Product 1

HCID 178513458HCID 178513458, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of EXAMPLE 12B (0.421 g, 0.897 mmol) and diisopropylethylamine (0.50 mL) in dichloromethane (5 mL) was treated with 4-chloro-3-nitrobenzenesulfonyl chloride (0.252 g, 0.99 mmol), stirred at room temperature for 24 hours and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient from 0%-10% methanol/dichloromethane to give the desired product (0.33 g, 60%). MS (ESI) m/e 614 (M−H)−.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified by silica gel chromatography
  3. washeluting with a gradient from 0%-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-f013e69740954d3ea41d549fb5c2cc16
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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