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

HRID 1833740Notes

Reaction equation

HRID 1833740 reaction equation
Cl.C(C1C=CC(C(N)=N)=CC=1)CCCCCC.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:36]([C:38]1[C:39](O)=[N:40][C:41]([C:44]2[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:46][CH:45]=2)=[N:42][CH:43]=1)#[N:37].P(Cl)(Cl)([Cl:60])=O>C(O)C>[Cl:60][C:39]1[C:38]([C:36]#[N:37])=[CH:43][N:42]=[C:41]([C:44]2[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:46][CH:45]=2)[N:40]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 15564097p-n-Heptylbenzamidine hydrochlorideHCID 178442520HCID 178442520, compound

Product 1

HCID 213888174-Chloro-5-cyano-2-(4-n-heptylphenyl)-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-heptylbenzamidine 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-heptylphenyl)-pyrimidine (melting point 195.6°-198.6° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-heptylphenyl)-pyrimidine having a melting point of 76.3°-76.8° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-59931aa883cd43818767139cd9f41090
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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