Benzenesulfonyl chloride, 3,4-dichloro- → HCID 30328636, compound

HRID 1868095Notes

Reaction equation

HRID 1868095 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[Cl:8][C:9]1[CH:10]=[C:11]([S:16](Cl)(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1[Cl:15].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([S:16]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)(=[O:17])=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

5

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one

Product 1

HCID 30328636HCID 30328636, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of piperazine-2-one (326.2 mg, 3.3 mmol) with 3,4-dichlorobenzene-sulfonyl chloride (800 mg, 3.3 mmol) was carried out according to a similar procedure described for example 15A using anhydrous dichloromethane (8 mL) as solvent and diisopropylethylamine (1.42 mL, 8.2 mmol) as base. 4-(3,4-dichloro-benzenesulfonyl)-piperazin-2-one was obtained in 90.3% yield (912 mg) as white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 3.17-3.24 (m, 2H) 3.25-3.30 (m, 2H) 3.59 (s, 2H) 7.79 (dd, J=8.46, 2.15 Hz, 1H) 7.94 (d, J=8.34 Hz, 1H) 8.06 (d, J=2.02 Hz, 1H) 8.08 (s, 1H).

Sources & evidence

ORD record
ord-74b28990d69d43e499fd74159bdaf0d6
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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