Hydrochloric Acid → 2-(4-Heptylphenyl)pyrimidine-5-carbonitrile

HRID 1833729Notes

Reaction equation

HRID 1833729 reaction equation
Cl.[CH2:2]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OC(=O)C(=COCC)C(OCC)=O)C.CC[O-].[Na+].C(O[C:39]([C:41]1[C:42](O)=[N:43]C(C2C=CC(CCCCCCC)=CC=2)=[N:45][CH:46]=1)=O)C.P(Cl)(Cl)(Cl)=O.C(OC(C1C(Cl)=NC(C2C=CC(CCCCCCC)=CC=2)=NC=1)=O)C>C(O)C>[C:46]([C:41]1[CH:39]=[N:14][C:13]([C:12]2[CH:11]=[CH:10][C:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:16][CH:15]=2)=[N:43][CH:42]=1)#[N:45]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 24813Phosphorus oxychlorideHCID 5758634-HeptylbenzonitrileHCID 2723922Sodium ethoxideHCID 538457562(-p-n-Heptylphenyl)-4-chloro-5-pyrimidinecarboxylic acid ethyl esterHCID 178442521HCID 178442521, compound

Product 1

HCID 213888332-(4-Heptylphenyl)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material can be obtained according to the procedure of A. B. Todd and F. Bergel, J. Chem. Soc. 1937, 366 from p-n-heptylbenzamie hydrochloride [prepared according to H. Schubert and H. Zaschke, J. prakt. Chem. 312, 494 (1970) from p-n-heptylbenzonitrile; melting point 126.0°-127.3° C[ and ethoxymethylenemalonic acid diethyl ester with sodium ethylate in ethanol and subsequent treatment of the obtained 2-(p-n-heptylphenyl)-4-hydroxy-5-primidinecarboxylic acid ethyl ester (melting point 184.7°-185.3° C) with phosphorus oxychloride. The melting point of 2(-p-n-heptylphenyl)-4-chloro-5-pyrimidinecarboxylic acid ethyl ester is 49.2°-49.8° C.

Workup

  1. customThe starting material can be obtained
  2. customis 49.2°-49.8° C.

Sources & evidence

ORD record
ord-2b2737df5f4442baa56fd96861fe0b99
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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