1,2-Dichloroethane → Benzonitrile, 4-[5-(4-butylphenyl)-2-pyrimidinyl]-

HRID 1448434Notes

Reaction equation

HRID 1448434 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=O)=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(Cl)CCl.P(Cl)(Cl)(Cl)=O>CCOCC>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[N:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:21]#[N:23])=[CH:24][CH:25]=3)=[N:13][CH:12]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 155640734-[5-(4-n-Butylphenyl)-2-pyrimidinyl] benzoic acid amide

Product 1

HCID 113397Benzonitrile, 4-[5-(4-butylphenyl)-2-pyrimidinyl]-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

102.75 G. of 4-[5-(4-n-butylphenyl)-2-pyrimidyl] benzoic acid amide are refluxed for 80 minutes in a mixture of 1500 ml. of ethylene chloride and 34 ml. of phosphorus oxychloride with stirring. The mixture, diluted with ether, is washed with 2-N sodium hydroxide solution and then with water until neutral. After evaporation of the organic phase, which has been dried over sodium sulfate, there is obtained 5-(4-n-butylphenyl)-2-(4-cyanophenyl)pyrimidine which is filtered on a short silica gel column and subsequently recrystallized from methylene chloride/methanol; melting point 94.7° C.; clearing point 246°-246.7° C.

Workup

  1. washis washed with 2-N sodium hydroxide solution
  2. customAfter evaporation of the organic phase, which
  3. dry with materialhas been dried over sodium sulfate

Sources & evidence

ORD record
ord-30a2fb631f92478e8d0b6796a9561373
Source dataset
uspto-grants-1979_12
Patent number
US04180475

Reaction notes

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