N,N-Diethylaniline → Acetonitrile, [(4-chloro-6-methyl-2-pyrimidinyl)thio]-

HRID 1605239Notes

Reaction equation

HRID 1605239 reaction equation
C(N(CC)C1C=CC=CC=1)C.O[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([S:20][CH2:21][C:22]([NH2:24])=O)[N:14]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([S:20][CH2:21][C:22]#[N:24])[N:14]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1784295362-[(6-methyl-4-oxo-1H-pyrimidin-2-yl)sulfanyl]acetamide

Product 1

HCID 12228966Acetonitrile, [(4-chloro-6-methyl-2-pyrimidinyl)thio]-

Procedure

To a solution of 19.4 g. (0.13 mole) of N,N-diethylaniline in 250 ml of phosphorus oxychloride was added 25.8 g (0.13 mole) of 2-(4-hydroxy-6-methyl-2-pyrimidinylthio)acetamide, the mixture was heated under reflux for 1 hour. The phosphorus oxychloride was removed in a rotary evaporator and the residue was poured onto 1 liter of cracked ice. The precipitate which resulted was collected, dried, and recrystallized from heptane to give 13.0 g. of pure white product, m.p. 62°-65°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe phosphorus oxychloride was removed in a rotary evaporator
  4. additionthe residue was poured onto 1 liter of cracked ice
  5. customThe precipitate which resulted
  6. customwas collected
  7. customdried
  8. customrecrystallized from heptane
  9. customto give 13.0 g

Sources & evidence

ORD record
ord-39dac443eaf14493a47f7c44a5fe066c
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

Loading…