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

HRID 1605240Notes

Reaction equation

HRID 1605240 reaction equation
O[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([S:11][CH2:12][C:13]([NH2:15])=O)[N:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([S:11][CH2:12][C:13]#[N:15])[N:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178439473HCID 178439473, compound

Product 1

HCID 12228980Acetonitrile, [(4-chloro-6-propyl-2-pyrimidinyl)thio]-

Procedure

To a suspension of 4.5 g. (0.02 mole) of 2-(4-hydroxy-6-propyl-2-pyrimidinylthio)acetamide in 50 ml of phosphorus oxychloride was added 2.98 g. of N,N-diethylaniline. The mixture was heated for ten minutes to reflux temperature. The phosphorus oxychloride was removed in a rotary evaporator and the residue was poured into 150 ml of ice-water. The water mixture was extracted with 100 ml of ether. The ether layer was dried over magnesium sulfate, filtered and evaporated in a rotary evaporator to give an oil. A small amount of the oil was dried in vacuo without purification to afford the analytical sample.

Workup

  1. additionTo a suspension of 4.5 g
  2. temperatureThe mixture was heated for ten minutes
  3. temperatureto reflux temperature
  4. customThe phosphorus oxychloride was removed in a rotary evaporator
  5. additionthe residue was poured into 150 ml of ice-water
  6. extractionThe water mixture was extracted with 100 ml of ether
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in a rotary evaporator
  10. customto give an oil
  11. customA small amount of the oil was dried in vacuo without purification
  12. customto afford the analytical sample

Sources & evidence

ORD record
ord-0ce43b25fd0e46ca89114acb0e991e03
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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