1,2-Dichloroethane → 4-[5-(4-Pentylphenyl)pyrimidin-2-YL]benzonitrile

HRID 461302Notes

Reaction equation

HRID 461302 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=O)=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)CCl.P(Cl)(Cl)(Cl)=O>CCOCC>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[N:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:24])=[CH:25][CH:26]=3)=[N:14][CH:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 155640744-(5-(4-Pentylphenyl)pyrimidin-2-yl)benzamide

Product 1

HCID 155640834-[5-(4-Pentylphenyl)pyrimidin-2-YL]benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.2 g. of 4-[5-(4-n-pentylphenyl)-2-pyrimidyl]-benzoic acid amide are reacted under reflux in a mixture of 200 ml. of ethylene chloride and 2.5 ml. of phosphorus oxychloride for 1 hour, with stirring. The reaction mixture is diluted with ether and washed with 2N sodium hydroxide solution and then with water until neutral. After evaporation of the organic phase, which has been dried over sodium sulfate, 5-(4-n-pentylphenyl)-2-(4-cyanophenyl)-pyrimidine is obtained and is filtered on a short silica gel column and subsequently recrystallized from methylene chloride/methanol, m.p. 125.5°; cl.p. 242.5°-243°.

Workup

  1. temperatureunder reflux in a mixture of 200 ml
  2. washwashed with 2N sodium hydroxide solution
  3. customAfter evaporation of the organic phase, which
  4. dry with materialhas been dried over sodium sulfate

Sources & evidence

ORD record
ord-4bb34a08ef3c44eb80b788415e2a0e17
Source dataset
uspto-grants-1977_12
Patent number
US04062798

Reaction notes

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