Chlorosuccinimide → HCID 18551158, compound

HRID 1698838Notes

Reaction equation

HRID 1698838 reaction equation
[OH:1][C:2]([C:28]([F:31])([F:30])[F:29])([CH2:16][C:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18])[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:11](=[O:12])[O:10][CH2:9]2)=[O:4].[Cl:32]N1C(=O)CCC1=O>CO>[Cl:32][C:24]1[CH:25]=[C:20]([C:17]([CH3:18])([CH3:19])[CH2:16][C:2]([OH:1])([C:28]([F:31])([F:29])[F:30])[C:3]([NH:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:11](=[O:12])[O:10][CH2:9]3)=[O:4])[CH:21]=[CH:22][C:23]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18551208HCID 18551208, compound

Product 1

HCID 18551158HCID 18551158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22 mg of 5-[2-hydroxy-4-(4-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeroylamino]-phthalide is stirred in 1.5 ml of methanol with 20 mg of N-chlorosuccinimide for 5 hours. The mixture is then dispersed in ice water, sodium bicarbonate solution and ethyl acetate, the ethyl acetate phase is dried, and it is concentrated by evaporation. 20 mg of 5-[4-(3-bromo-4-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeroylamino]-phthalide, which melts after recrystallization from isopropyl ether at 189-191° C., is thus obtained.

Workup

  1. dry with materialsodium bicarbonate solution and ethyl acetate, the ethyl acetate phase is dried
  2. concentrationit is concentrated by evaporation
  3. customafter recrystallization from isopropyl ether at 189-191° C.
  4. customis thus obtained

Sources & evidence

ORD record
ord-64bc30a86eb248f6a88ef9636fe679fd
Source dataset
uspto-grants-2002_02
Patent number
US06344454B1

Reaction notes

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