Sodium Hydroxide → 4-Chloro-5-cyano-2-(4-heptyloxyphenyl)-pyrimidine

HRID 1973617Notes

Reaction equation

HRID 1973617 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[NH:15])=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O[C:22](=O)[C:23](=[CH:26]OCC)[C:24]#[N:25])C.CC[O-].[Na+].[OH-].[Na+].P(Cl)(Cl)([Cl:39])=O>C(O)C>[Cl:39][C:26]1[C:23]([C:24]#[N:25])=[CH:22][N:16]=[C:14]([C:13]2[CH:17]=[CH:18][C:10]([O:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=2)[N:15]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 12238503p-Heptyloxybenzamidine hydrochloride

Product 1

HCID 213888064-Chloro-5-cyano-2-(4-heptyloxyphenyl)-pyrimidine

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, 365 by reaction of p-n-heptyloxybenzamidine hydrochloride with α-ethoxymethylene-α-cyanoacetic acid ethyl ester and sodium ethylate in ethanol and then with sodium hydroxide solution. The resulting 5-cyano-4-hydroxy-2-(4-n-heptyloxphenyl)-pyrimidine (melting point 180.8° C; smectic up to 231.5° C. (clearing point)) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-heptyloxyphenyl)-pyrimidine having a melting point of 133.3°-134.6° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-fee15190b7f74cddbee8610362ba37d6
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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