Chlorosuccinimide → HCID 15871397, compound

HRID 1740854Notes

Reaction equation

HRID 1740854 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH2:15][C:16]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH:3]=1.[Cl:26]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:26][C:3]1[C:4]([NH:14][CH2:15][C:16]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])=[N:5][C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 218334642-(6-methyl-2-phenyl-4-pyrimidinylamino)-N-methyl-N-phenylacetamide

Product 1

HCID 15871397HCID 15871397, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(6-methyl-2-phenyl-4-pyrimidinylamino)-N-methyl-N-phenylacetamide (1.0 g) obtained in Example 88, N-chlorosuccinimide (0.44 g) and acetic acid (15 ml) is heated with stirring at 90° C. for three hours, and the reaction mixture is concentrated under reduced pressure. To the residue is added ice-water (30 ml) with stirring, and the precipitates are collected by filtration, washed with water, and recrystallized from isopropanol to give the desired compound (1.1 g), m.p. 154-155° C.

Workup

  1. temperatureis heated
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionTo the residue is added ice-water (30 ml)
  4. stirringwith stirring
  5. filtrationthe precipitates are collected by filtration
  6. washwashed with water
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-e9ea2e92d61b407f96e6fea011ef5b1d
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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