Ethyl 2-cyano-2-(hydroxyimino)acetate → HCID 136062367, compound

HRID 1288282Notes

Reaction equation

HRID 1288282 reaction equation
Cl.[C:2]1([CH2:8][CH2:9][C:10]([NH2:12])=[NH:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[N:16](=[C:18]([C:24]#[N:25])[C:19](OCC)=[O:20])[OH:17]>>[NH2:25][C:24]1[N:11]=[C:10]([CH2:9][CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:12][C:19](=[O:20])[C:18]=1[N:16]=[O:17]

Participants

4

Reactant 3

HCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 10942334Sodium MethoxideHCID 126219883-Phenylpropanimidamide--hydrogen chloride (1/1)

Product 1

HCID 136062367HCID 136062367, compound

Procedure

3-Phenylpropionamidine hydrochloride (4.33 g; prepared as described by P. W. Neber and A. Uber, Leibig's Annalen der Chemie, 1928, 467, 52) was added to a solution of sodium methoxide (prepared from 2.17 g. sodium and 37 ml. anhydrous methanol). Ethyl α-oximinocyanoacetate (3.34 g.) was added, and the mixture was refluxed with stirring for 5.25 hours and left to stand overnight. The mauve solid was filtered off and washed with a small quantity of anhydrous methanol to give the crude sodium salt of 4-amino-5-nitroso-2-(2-phenylethyl)pyrimid-6-one (3.9 g.). An aliquot was dissolved in water, and the solution was filtered and acidified to pH 4 with glacial acetic acid to give 4-amino-5-nitroso-2-(2-phenylethyl)pyrimid-6-one as a turquoise solid, m.p. 253° C. (with decomposition, sintering at 188° C.).

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed
  3. waitleft
  4. waitto stand overnight
  5. filtrationThe mauve solid was filtered off
  6. washwashed with a small quantity of anhydrous methanol

Sources & evidence

ORD record
ord-10ec1901795c422cb4467310caf9e1cd
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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