Water → HCID 136354623, compound

HRID 1288290Notes

Reaction equation

HRID 1288290 reaction equation
Cl.[CH2:2]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH2:14])=[NH:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:18](=[C:20]([C:26]#[N:27])[C:21](OCC)=[O:22])[OH:19].[Na].O>C(O)C.C(O)(=O)C>[NH2:27][C:26]1[N:13]=[C:12]([C:11]2[CH:15]=[CH:16][CH:17]=[C:9]([CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:10]=2)[NH:14][C:21](=[O:22])[C:20]=1[N:18]=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 21504358HCID 21504358, compound

Product 1

HCID 136354623HCID 136354623, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

3-Benzylbenzamidine hydrochloride (12.3 g.) and ethyl α-oximinocyanoacetate (7.1 g.) were added to a solution of sodium (4.6 g.) in anhydrous ethanol (60 ml.). The mixture was heated under reflux with stirring for 5 hours and then allowed to stand at room temperature overnight. The mixture was poured into water (600 ml.), acidified to pH 5 with glacial acetic acid and chilled for 3 hours. The solid obtained was filtered off and washed with water to give 4-amino-2-(3-benzylphenyl)-5-nitrosopyrimid-6-one (11.95 g.), m.p. 145°-148° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. waitto stand at room temperature overnight
  4. temperaturechilled for 3 hours
  5. customThe solid obtained
  6. filtrationwas filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-2f4d90c9489a46ec87c5bd054e2372e5
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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