Sodium Hydroxide → HCID 21388851, compound

HRID 1973609Notes

Reaction equation

HRID 1973609 reaction equation
Cl.C(OC1C=CC(C(N)=N)=CC=1)C.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:32]([C:34]1[C:35](O)=[N:36][C:37]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH3:48])=[CH:42][CH:41]=2)=[N:38][CH:39]=1)#[N:33].P(Cl)(Cl)([Cl:52])=O>C(O)C>[Cl:52][C:35]1[C:34]([C:32]#[N:33])=[CH:39][N:38]=[C:37]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH3:48])=[CH:42][CH:41]=2)[N:36]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 12238507HCID 12238507, compoundHCID 178466131HCID 178466131, compound

Product 1

HCID 21388851HCID 21388851, 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-ethoxybenzamidine 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-ethoxyphenyl)-pyrimidine (melting point 288.6°-290.5° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-ethoxyphenyl)-pyrimidine having a melting point of 190.6°-192.4° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-4fafa597da284ff982b0e885842663f7
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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