1,2-Dichloroethane → Benzonitrile, 4-(5-heptyl-2-pyrimidinyl)-

HRID 461307Notes

Reaction equation

HRID 461307 reaction equation
C([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=O)=[CH:16][CH:15]=2)[N:9]=1)CCCCCC.[CH2:23](Cl)[CH2:24]Cl.P(Cl)(Cl)(Cl)=O>CCOCC>[CH2:16]([C:13]1[CH:12]=[N:11][C:10]([C:14]2[CH:15]=[CH:16][C:17]([C:18]#[N:20])=[CH:21][CH:22]=2)=[N:9][CH:8]=1)[CH2:15][CH2:14][CH2:22][CH2:21][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 538442864-(4-n-Heptylpyrimid-2-yl)benzoic acid amide

Product 1

HCID 108846Benzonitrile, 4-(5-heptyl-2-pyrimidinyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.9 g. of 4-(4-n-heptylpyrimid-2-yl)benzoic acid amide are left for 80 minutes under reflux in a mixture of 40 ml. of ethylene chloride and 0.63 ml. of phosphorus oxychloride, with stirring. The reaction mixture, diluted with ether, is washed with 2N sodium hydroxide solution and then with water until neutral. After evaporation of the organic phase, drying over sodium sulfate, 1.9 g. of 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine result, which are distilled in a high vacuum, having a m.p. of 44.2°-44.7°; cl.p. 50.1°-50.4°.

Workup

  1. temperatureunder reflux in a mixture of 40 ml
  2. washis washed with 2N sodium hydroxide solution
  3. customAfter evaporation of the organic phase
  4. dry with materialdrying over sodium sulfate, 1.9 g

Sources & evidence

ORD record
ord-aa5edd4b8d9c45928ad767ebc30ae839
Source dataset
uspto-grants-1977_12
Patent number
US04062798

Reaction notes

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