Chloroacetyl chloride → N-(4,6-dimethoxypyrimidin-5-yl)chloroacetamide

HRID 542386Notes

Reaction equation

HRID 542386 reaction equation
[NH2:1][C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].[Cl:12][CH2:13][C:14](Cl)=[O:15]>C(Cl)Cl>[CH3:11][O:10][C:3]1[C:2]([NH:1][C:14](=[O:15])[CH2:13][Cl:12])=[C:7]([O:8][CH3:9])[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 28179794,6-Dimethoxypyrimidin-5-amine

Product 1

HCID 15585336N-(4,6-dimethoxypyrimidin-5-yl)chloroacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sulphonation flask is charged with 310 g 5-amino-4,6-dimethoxypyrimidin and 3500 ml dry CH2Cl2. To this mixture is added, within 15 minutes, a solution of 248.6 g chloroacetyl chloride in 400 ml dry CH2Cl2. The reaction is exothermic, the temperature rises from 14° to 32° and a suspension is formed. The reaction mixture is heated under reflux for 2 hours, then cooled to ambient temperature and evaporated till dryness. The solid residue is suspended in 3 l ice water, the suspension adjusted at pH 7-8 with diluted NaOH, cooled to 5° and sucked-off. The precipitate is washed twice with 500 ml ice water and then dried in vacuum at 60° to give the title compound, m.p. 193°-195°.

Workup

  1. additionTo this mixture is added, within 15 minutes
  2. customrises from 14° to 32°
  3. customa suspension is formed
  4. temperatureThe reaction mixture is heated
  5. temperatureunder reflux for 2 hours
  6. customevaporated till dryness
  7. temperaturecooled to 5°
  8. washThe precipitate is washed twice with 500 ml ice water
  9. customdried in vacuum at 60°

Sources & evidence

ORD record
ord-a82ed227ee60475cb45998e02ccc696a
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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