Sodium Hydroxide → HCID 21388822, compound

HRID 1973601Notes

Reaction equation

HRID 1973601 reaction equation
Cl.C(C1C=CC(C(N)=N)=CC=1)CCC.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]([CH2:47][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]([CH2:47][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 15564093HCID 15564093, compoundHCID 178440773HCID 178440773, compound

Product 1

HCID 21388822HCID 21388822, 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-butylbenzamidine 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-butylphenyl)-pyrimidine (melting point 230.3°-231.3° C.) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-butylphenyl)-pyrimidine having a melting point of 106.8°-107.0° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-63b27b8dbd9a4f469f9512aea658b94c
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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