Phosphorus oxychloride → 4-Chloro-2-(3-tolyl)-pyrimidine

HRID 1380052Notes

Reaction equation

HRID 1380052 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11](O)[CH:10]=[CH:9][N:8]=2)[CH:2]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:3]2[CH:2]=[C:1]([CH3:14])[CH:6]=[CH:5][CH:4]=2)[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424659HCID 178424659, compound

Product 1

HCID 135903674-Chloro-2-(3-tolyl)-pyrimidine

Procedure

A 23.91 g portion of 2-(3-tolyl)-4-pyrimidinol was mixed with 400 ml of phosphorous oxychloride in a one liter round bottom flask, under a drying tube and heated on a steam bath overnight. The mixture was allowed to cool and then poured over 2 liters of ice. The resulting solid was collected, washed with 50 ml of ether, dried and recrystallized from 100 ml of ethanol, giving 16.23 g of the desired intermediate, mp 74°-75° C.

Workup

  1. temperatureheated on a steam bath overnight
  2. temperatureto cool
  3. customThe resulting solid was collected
  4. washwashed with 50 ml of ether
  5. customdried
  6. customrecrystallized from 100 ml of ethanol

Sources & evidence

ORD record
ord-8b0440ca22d448daab24804e0d359175
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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