Water → HCID 136354614, compound

HRID 1288261Notes

Reaction equation

HRID 1288261 reaction equation
C[O-].[Na+].Cl.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH2:11])=[NH:10].[N:16](=[C:18]([C:24]#[N:25])[C:19](OCC)=[O:20])[OH:17].O>CO.C(O)(=O)C>[NH2:25][C:24]1[N:10]=[C:9]([C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6][CH3:5])[NH:11][C:19](=[O:20])[C:18]=1[N:16]=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 10942334Sodium MethoxideHCID 122542242-Methoxy-benzamidine hydrochloride

Product 1

HCID 136354614HCID 136354614, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A stirred solution of sodium methoxide in dry methanol [prepared from sodium (10.7 g.) and dry methanol (150 ml.)] maintained at 0° C. was treated with 2-methoxybenzamidine hydrochloride (21.6 g.) followed by ethyl α-oximinocyanoacetate (16.5 g.). The mixture was then heated to reflux with stirring for 4.5 hours, and then poured into water (1000 ml.) and brought to pH6 by the addition of glacial acetic acid. The resultant green solid was filtered off and recrystallised from aqueous acetic acid to give 4-amino-2-(2-methoxyphenyl)-5-nitrosopyrimid-6-one (19.2 g.), m.p. 210°-211° C. (with decomposition). A further quantity of less pure 4-amino-2-(2-methoxyphenyl)-5-nitrosopyrimid-6-one (2.9 g.) was obtained by concentration of the mother liquors of the recrystallisation.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux
  3. filtrationThe resultant green solid was filtered off
  4. customrecrystallised from aqueous acetic acid

Sources & evidence

ORD record
ord-c300dfd9c24c46b9b18a53d625da2c9f
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

Loading…