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

HRID 370076Notes

Reaction equation

HRID 370076 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-6a5d609db4a14b8da882832c83aea8d3
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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