Sodium Hydroxide → HCID 21388785, compound

HRID 1833749Notes

Reaction equation

HRID 1833749 reaction equation
Cl.C(OC1C=CC(C(N)=N)=CC=1)CCCCC.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]([O: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]([O: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 12238501p-n-Hexyloxybenzamidine hydrochlorideHCID 178444932HCID 178444932, compound

Product 1

HCID 21388785HCID 21388785, 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-hexyloxybenzamidine 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-hexyloxyphenyl)-pyrimidine (melting point 193.0° C; smectic up to 226.0° (clearing point)) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-hexyloxyphenyl)-pyrimidine having a melting point of 132.7°-133.1° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-fe9415e6cd3546278f596da5b19fd4a1
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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