Sodium Hydroxide → HCID 21388802, compound

HRID 1833744Notes

Reaction equation

HRID 1833744 reaction equation
Cl.C(OC1C=CC(C(N)=N)=CC=1)CC.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:33]([C:35]1[C:36](O)=[N:37][C:38]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH3:50])=[CH:43][CH:42]=2)=[N:39][CH:40]=1)#[N:34].P(Cl)(Cl)([Cl:54])=O>C(O)C>[Cl:54][C:36]1[C:35]([C:33]#[N:34])=[CH:40][N:39]=[C:38]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH3:50])=[CH:43][CH:42]=2)[N:37]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 122385104-Propoxybenzimidamide hydrochlorideHCID 178458264HCID 178458264, compound

Product 1

HCID 21388802HCID 21388802, compound

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-propoxybenzamidine 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-propoxyphenyl)-pyrimidine (melting point 255.3°-256.5° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-propoxyphenyl)-pyrimidine having a melting point of 193.3°-194.4° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-2c2eedcbe3b44b8b8821ce1753134a30
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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