Chlorosuccinimide → HCID 20080819, compound

HRID 1653842Notes

Reaction equation

HRID 1653842 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[NH:15][C:14]=3[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Cl:24]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:24][C:17]1[C:18](=[O:19])[C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:12][CH:11]=2)=[C:14]([CH3:21])[NH:15][C:16]=1[CH3:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20080785HCID 20080785, compound

Product 1

HCID 20080819HCID 20080819, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 3-(4-(4-chlorophenoxy)phenyl)-2,6-dimethylpyridin-4(1H)-one (0.8 g) in acetic acid (10 ml) was added N-chlorosuccinimide (0.39 g). The mixture was heated at 100° for 30 min, cooled to room temperature and the precipitate filtered and dried in vacuo to afford the title compound (0.33 g), m.p. 340°-343°, NMR δH (d6 -DMSO) 11.3 (1H, br.s), 7.42 (2H, m), 7.2 (2H, m), 6.95-7.12 (4H, m), 2.4 (3H, s), 2.1 (3H, s).

Workup

  1. temperatureThe mixture was heated at 100° for 30 min
  2. filtrationthe precipitate filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-edfe9b9f266247ab932b0426ad27f4dc
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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