Benzoyl Peroxide → N-(4-chlorophenyl)-2-[((5-(bromomethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

HRID 2300906Notes

Reaction equation

HRID 2300906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:21][C:22]([CH3:26])=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:4][CH:3]=1.[Br:28]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:21][C:22]([CH2:26][Br:28])=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 183767483-chloro-N-{4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl}-5-methylthiophene-2-carboxamide

Product 1

HCID 18376771N-(4-chlorophenyl)-2-[((5-(bromomethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamideYield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of N-(4-chlorophenyl)-2-[((5-methyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (2.6 g, 6.0 mmol) in dry benzene (250 mL) were added N-bromosuccinimide (1.2 g, 6.6 mmol) and benzoyl peroxide (0.15 g, 0.6 mmol). The mixture was refluxed while irradiating with a 250 Watt lamp. After 28 hours the reaction was concentrated of all volatiles in vacuo and the resulting solid triturated with benzene. Purification by flash chromatography on silica gel afforded 2.3 g (75% yield) of N-(4-chlorophenyl)-2-[((5-bromomethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide as a white solid; NMR (DMSO-d6) 11.1 (s, 1), 10.7 (s, 1), 8.3 (d, 1), 7.9 (s, 1), 7.7 (d, 2), 7.6 (d, 1), 7.4 (d, 2), 7.3 (s, 1), 4.9 (s, 2) ppm.

Workup

  1. temperatureThe mixture was refluxed
  2. customwhile irradiating with a 250 Watt lamp
  3. concentrationAfter 28 hours the reaction was concentrated of all volatiles in vacuo
  4. customthe resulting solid triturated with benzene
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7f44319ba4e74b6fbbdf00c07936098b
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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