Ethanol → HCID 86742227, compound

HRID 580216Notes

Reaction equation

HRID 580216 reaction equation
[Cl-].[NH4+:2].[CH3:3][O:4][N:5]=[C:6]([C:9]#[N:10])[C:7]#[N:8].[CH2:11]([OH:13])[CH3:12]>N>[C:11]([O-:4])(=[O:13])[CH3:12].[C:7]([C:6](=[N:5][O:4][CH3:3])[C:9]([NH2:2])=[NH2+:10])#[N:8]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 25517Ammonium ChlorideHCID 12474891Methoxycarbonimidoyl dicyanide

Product 1

HCID 86742227HCID 86742227, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of ammonium chloride (28.4 g 0.53 mole) in 28% aqueous ammonia (355 ml) and ethanol (180 ml) was added dropwise a solution of 2-methoxyiminopropanedinitrile (58.0 g, 0.53 mole) in ethanol (120 ml) at -15° to -10° C. over a period of 30 minutes, with stirring. The mixture was stirred at -10° C. overnight and then at ambient temperature (20°-25° C.) for one day. The reaction mixture was partitioned between water (350 ml) and CH2Cl2 (350 ml), and the aqueous phase was saturated with sodium chloride, and extracted again with CH2Cl2 (300 ml). The organic extracts were combined, dried over MgSO4 and evaporated in vacuo. A solution of the residue in ethyl acetate (1.6 L) was adjusted to pH 3-4 with acetic acid to precipitate the title compound as crystals, which were collected by filtration and washed with ethyl acetate. Yield 67.6 g (69%). M.p. 152°-4° C. (dec.). [Lit., m.p. 150°-155° C. (dec.)].

Workup

  1. stirringThe mixture was stirred at -10° C. overnight
  2. customThe reaction mixture was partitioned between water (350 ml) and CH2Cl2 (350 ml)
  3. extractionextracted again with CH2Cl2 (300 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto precipitate the title compound as crystals, which
  7. filtrationwere collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-eb7d335c3c3b495f91b7e397a9b2739c
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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