Ethylamine → 4,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile

HRID 1757889Notes

Reaction equation

HRID 1757889 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([Cl:11])[N:3]=1.[CH2:12]([NH2:14])[CH3:13]>CC(C)=O>[Cl:11][C:4]1[C:5]([C:9]#[N:10])=[C:6]([Cl:8])[N:7]=[C:2]([NH:14][CH2:12][CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 205102564,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 12.9 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile in 150 ml of acetone was cooled to -10°, and 7.7 grams of an aqueous 70% ethylamine solution was added dropwise during 2 hours. The temperature of the reaction mixture was maintained at -10° throughout the addition. Following complete addition, the reaction mixture was allowed to warm to room temperature, where it stood for 16 hours. Then most of the acetone was removed by evaporation under reduced pressure. The residue was extracted with a mixture of water and diethyl ether. The ether layer was separated and dried over magnesium sulfate. The dried ether layer was filtered, and the ether was removed under reduced pressure. The residue was recrystallized from a mixture of methylcyclohexane and benzene, then from carbon tetrachloride, to give 4.2 grams of 4,6-dichloro-2- ethylamino-5-pyrimidinecarbonitrile; mp, 145°-150°.

Workup

  1. temperatureThe temperature of the reaction mixture was maintained at -10° throughout the addition
  2. additionaddition
  3. customThen most of the acetone was removed by evaporation under reduced pressure
  4. extractionThe residue was extracted with a mixture of water and diethyl ether
  5. customThe ether layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe dried ether layer was filtered
  8. customthe ether was removed under reduced pressure
  9. customThe residue was recrystallized from a mixture of methylcyclohexane and benzene

Sources & evidence

ORD record
ord-8dda806c88064b25898f344c54993db2
Source dataset
uspto-grants-1983_02
Patent number
USRE031136

Reaction notes

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