Triethylamine → HCID 53866493, compound

HRID 647114Notes

Reaction equation

HRID 647114 reaction equation
Cl.[C:2]([C:5](=[N:10][O:11][CH2:12][CH3:13])[C:6]([O:8][CH3:9])=[O:7])(=[NH:4])[NH2:3].Cl[C:15](=[CH2:18])[C:16]#[N:17].C(N(CC)CC)C>C(O)C>[CH2:12]([O:11][N:10]=[C:5]([C:2]1[N:3]=[C:16]([NH2:17])[CH:15]=[CH:18][N:4]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 73674330HCID 73674330, compound

Product 1

HCID 53866493HCID 53866493, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-amidino-2-ethoxyiminoacetate hydrochloride (syn isomer) (2.1 g), 2-chloroacrylonitrile (875 mg) and triethylamine (2.0 g) in ethanol (21 ml) was stirred for 8 hours at ambient temperature and allowed to stand at the same temperature overnight. The mixture was evaporated to dryness and the residue was dissolved in a mixture of ethyl acetate (20 ml) and water (10 ml). The organic layer was separated out, treated with activated charcoal and evaporated to dryness. The residue was purified by a column chromatography on silica gel (30 g) using ethyl acetate-benzene (1:1) as an eluant to give a mixture (1.0 g) of methyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) and ethyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) (1:1). mp 105° to 110° C.

Workup

  1. customto stand at the same temperature overnight
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate (20 ml) and water (10 ml)
  4. customThe organic layer was separated out
  5. additiontreated with activated charcoal
  6. customevaporated to dryness
  7. customThe residue was purified by a column chromatography on silica gel (30 g)

Sources & evidence

ORD record
ord-2288c8109df64d55874ee5d9408636fc
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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