Chlorosuccinimide → HCID 9824265, compound

HRID 1167629Notes

Reaction equation

HRID 1167629 reaction equation
[CH3:1][N:2]([CH3:29])[C:3](=[O:28])[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]=[C:8]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:7]=1.[Cl:30]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:30][C:11]1[C:6]([NH:5][CH2:4][C:3]([N:2]([CH3:29])[CH3:1])=[O:28])=[N:7][C:8]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)=[N:9][C:10]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 9822304HCID 9822304, compound

Product 1

HCID 9824265HCID 9824265, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N,N-dimethyl-2-[6-phenyl-2-(4-trifluoromethyl-phenyl)-4-pyrimidinylamino]acetamide (15.9 g), N-chlorosuccinimide (6.4 g) and acetic acid (80 ml) is stirred at 90° C. for 1.5 hour. The reaction mixture is concentrated under reduced pressure, and water and chloroform are added to the residue. The mixture is neutralized with an aqueous sodium hydroxide solution (1 mol/L), and the chloroform layer is separated. The chloroform layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to give the desired compound (16 g).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, and water and chloroform
  2. additionare added to the residue
  3. customthe chloroform layer is separated
  4. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue is purified by silica gel column chromatography (eluent: chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6695321df8184c1eaca4dba15c12fe03
Source dataset
uspto-grants-2003_09
Patent number
US06620817B1

Reaction notes

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