Methanol → N-(4-chlorophenyl)-2-[((5-methoxycarbonyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

HRID 370121Notes

Reaction equation

HRID 370121 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[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]([CH:26]=[O:27])=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:4][CH:3]=1.BrN1[C:34](=[O:35])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.CO>C(Cl)(Cl)(Cl)Cl.C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:28])[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]([C:26]([O:35][CH3:34])=[O:27])=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18376694N-(4-chlorophenyl)-2-[((5-formyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

Product 1

HCID 18376654N-(4-chlorophenyl)-2-[((5-methoxycarbonyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamideYield 80.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(4-chlorophenyl)-2-[((5-formyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (0.31 g, 0.69 mmol) in CCl4 (10 mL) and benzene (15 mL) was added N-bromosuccinimide (NBS) (0.18 g, 1.03 mmol) and 2,2'-azobisisobutyronitrile (AIBN) (0.011 g, 0.068 mmol). The reaction mixture was heated to reflux for 1 hour, and the resulting clear yellow solution was cooled to 0° C. Methanol (0.1 mL) was added and the reaction mixture was stirred for 14 hours at ambient temperature. Water was added and the reaction mixture was extracted with methylene chloride. The combined extracts were dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash chromatography on silica to afford 0.27 g of N-(4-chlorophenyl)-2-[((5-methoxycarbonyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide. as a pale yellow solid; NMR (DMSO-d6 /TFA) 11.3 (s,1), 10.8 (s, 1), 8.3 (d, 1), 7.9 (s, 1), 7.7 (m, 3), 7.6 (d, 1), 7.4 (d, 2), 3.8 (s, 3) ppm.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. extractionthe reaction mixture was extracted with methylene chloride
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-c79af217e9de4876993a878760d7d168
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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