Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 24884785, compound

HRID 901959Notes

Reaction equation

HRID 901959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[Cl:16][C:17]1[C:21]([CH2:22][NH:23][CH3:24])=[CH:20][S:19][C:18]=1[C:25]([N:27]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH2:29][CH2:28]1)=[O:26].C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[C:21]([CH2:22][N:23]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=2)(=[O:10])=[O:9])[CH3:24])=[CH:20][S:19][C:18]=1[C:25]([N:27]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH2:29][CH2:28]1)=[O:26]

Participants

5

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8471TriethylamineHCID 69211126HCID 69211126, compound

Product 1

HCID 24884785HCID 24884785, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitrobenzenesulfonyl chloride (0.46 g, 1.8 mmol) was added to a solution of 4-(3-chloro-4-(methylaminomethyl)thiophene-2-carbonyl)benzomorpholine hydrochloride (0.54 g, 1.49 mmol) and triethylamine (0.50 ml, 0.36 g, 3.6 mmol) in dichloromethane (20 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was reduced and chromatographed to afford 4-(3-chloro(N-(4-chloro-3-nitrobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carbonyl)benzomorpholine (0.61 g, 76%) as a white crystalline solid.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. customchromatographed

Sources & evidence

ORD record
ord-4638bb570d9d4fb4b2b5e5d09ffd8d26
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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