p-Bromobenzenesulfonyl chloride → 4-bromo-N-methyl-N-(3-(1,2,3,4-tetrahydroquinoxalin-3-one-1-carbonyl)benzyl)-benzenesulphonamide

HRID 901965Notes

Reaction equation

HRID 901965 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22](=[O:30])[CH2:21]1)=[O:19].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH3:12])[CH2:14][C:15]2[CH:33]=[CH:32][CH:31]=[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][C:22](=[O:30])[CH2:21]3)=[O:19])[CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 858677023-(Methylaminomethyl)benzoyl-1,2,3,4-tetrahydroquinoxalin-3-one

Product 1

HCID 597005924-bromo-N-methyl-N-(3-(1,2,3,4-tetrahydroquinoxalin-3-one-1-carbonyl)benzyl)-benzenesulphonamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromobenzenesulphonyl chloride (29 mg, 0.11 mmol) was added to a solution of 1-(3-(methylaminomethyl)benzoyl-1,2,3,4-tetrahydroquinoxalin-3-one (30 mg, 0.10 mmol) in dichloromethane (10 ml). The pH was adjusted to pH9 with triethylamine and the mixture stirred for 18 h. The mixture was reduced in vacuo, taken up in ethyl acetate, washed with water and brine, dried and reduced. Chromatography (50% EtOAc/50% 60-80 pet ether) afforded 4-bromo-N-methyl-N-(3-(1,2,3,4-tetrahydroquinoxalin-3-one-1-carbonyl)benzyl)-benzenesulphonamide (34 mg, 60%) as a white solid.

Workup

  1. washwashed with water and brine
  2. customdried

Sources & evidence

ORD record
ord-c1d9f788ffb84ce1aa20475142fd2362
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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