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

HRID 1833751Notes

Reaction equation

HRID 1833751 reaction equation
Cl.C(OC1C=CC(C(N)=N)=CC=1)CCCCCC.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:37]([C:39]1[C:40](O)=[N:41][C:42]([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[CH:47][CH:46]=2)=[N:43][CH:44]=1)#[N:38].P(Cl)(Cl)([Cl:62])=O>C(O)C>[Cl:62][C:40]1[C:39]([C:37]#[N:38])=[CH:44][N:43]=[C:42]([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[CH:47][CH:46]=2)[N:41]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 12238503p-Heptyloxybenzamidine hydrochlorideHCID 1784440455-Cyano-4-hydroxy-2-(4-n-heptyloxyphenyl)-pyrimidine

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-heptyloxyphenyl)-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-n-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-04f47dc09cd247f8a7f001584fb989b4
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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