Water → HCID 136354627, compound

HRID 1288300Notes

Reaction equation

HRID 1288300 reaction equation
[N:1](=[C:3]([C:9]#[N:10])[C:4](OCC)=[O:5])[OH:2].[Na].[Cl:12][C:13]1[C:14]([O:23][CH3:24])=[C:15]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:16]([NH2:18])=[NH:17].O>CO.C(O)(=O)C>[NH2:10][C:9]1[N:17]=[C:16]([C:15]2[CH:19]=[C:20]([Cl:22])[CH:21]=[C:13]([Cl:12])[C:14]=2[O:23][CH3:24])[NH:18][C:4](=[O:5])[C:3]=1[N:1]=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 21504418HCID 21504418, compound

Product 1

HCID 136354627HCID 136354627, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Ethyl α-oximinocyanoacetate (21 g.) was added to a solution of sodium (11.3 g.) in anhydrous methanol (300 ml.). Crude 3,5-dichloro-2-methoxybenzamidine (24 g.) dissolved in a little anhydrous methanol was added, and the mixture was heated to reflux with stirring for 8 hours. The mixture was poured into water (2000 ml.) and acidified with glacial acetic acid. The solid obtained was filtered off, washed with water and recrystallised from glacial acetic acid to give 4-amino-2-(3,5-dichloro-2-methoxyphenyl)-5-nitrosopyrimid-6-one (6.8 g.), m.p. 265° C. (with decomposition).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. customThe solid obtained
  5. filtrationwas filtered off
  6. washwashed with water
  7. customrecrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-2a9a00fc34294efa8386a147bc3deb31
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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