Chlorosuccinimide → GW 844520

HRID 1653849Notes

Reaction equation

HRID 1653849 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:20](=[O:21])[CH:19]=[C:18]([CH3:22])[NH:17][C:16]=3[CH3:23])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[Cl:28]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:28][C:19]1[C:20](=[O:21])[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:26])[F:27])=[CH:25][CH:24]=3)=[CH:14][CH:13]=2)=[C:16]([CH3:23])[NH:17][C:18]=1[CH3:22]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20080781HCID 20080781, compound

Product 1

HCID 9887751GW 844520Yield 24.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-(4-(4-trifluoromethoxyphenoxy)phenyl)-2,6-dimethylpyridin-4(1H)-one (0.37 g) and N-chlorosuccinimide (0.16 g) in chloroform was stirred at room temperature for 3 days. The precipitate was filtered off and recrystallised from DMF to afford the title compound (0.1 g), m.p. 298°-302°, NMR δH (d6 -DMSO) 7.35-7.5 (2H, m), 7.1-7.3 (4H, m), 7-7.1 (2H, m), 2.38 (3H, s), 2.1 (3H, s).

Workup

  1. filtrationThe precipitate was filtered off
  2. customrecrystallised from DMF

Sources & evidence

ORD record
ord-bb4b0ae79421485aa6f1e7981c6a40fa
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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