Diethyl (ethoxymethylene)malonate → 2-(4-Heptylphenyl)pyrimidine-5-carbonitrile

HRID 1973596Notes

Reaction equation

HRID 1973596 reaction equation
Cl.[CH2:2]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=O)=[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:40]([C:42]1[C:43](O)=[N:44]C(C2C=CC(CCCCCCC)=CC=2)=[N:46][CH:47]=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:47]([C:42]1[CH:40]=[N:15][C:13]([C:12]2[CH:16]=[CH:17][C:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)=[N:44][CH:43]=1)#[N:46]

Participants

8

Reactant 6

HCID 6871Diethyl (ethoxymethylene)malonateHCID 24813Phosphorus oxychlorideHCID 2723922Sodium ethoxideHCID 21491331p-n-Heptylbenzamide hydrochlorideHCID 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. R. Todd and F. Bergel, J. Chem. Soc. 1937, 366 from p-n-heptylbenzamide 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-pyrimidinecarboxylic 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-5d194f57318f4b829eef553348f24af0
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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