Chlorosuccinimide → HCID 18551158, compound

HRID 1066953Notes

Reaction equation

HRID 1066953 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-1b337b461a814fdd830f5ffe638c1ec6
Source dataset
uspto-grants-2001_06
Patent number
US06245804B1

Reaction notes

Loading…