Sodium Cyanide → HCID 69477110, compound

HRID 2275861

Reaction equation

HRID 2275861 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:13]#[N:14].[Na+].[Cl-].[NH4+:17]>N.CO.ClCCl>[NH2:17][C:10]([CH3:12])([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]#[N:14]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 36912841-(Benzyloxy)propan-2-one

Product 1

HCID 69477110HCID 69477110, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5.07 g (27.79 mmol) of 1-(benzyloxy)acetone were initially charged in 55.6 ml of 2 N aqueous ammonia in methanol, 1.53 g (31.12 mmol) of sodium cyanide and 3.71 g (31.12 mmol) of ammonium chloride were added and the mixture was heated under reflux for 2 h. Another 27.4 ml of 2 N aqueous ammonia in methanol were then added, and the reaction mixture was stirred under reflux for 2 h. The reaction solution was cooled and diluted with 90 ml of dichloromethane. The solid obtained was filtered off and the filtrate was concentrated. The residue was purified using silica gel (mobile phase: cyclohexane/ethyl acetate gradient: from 4/1 to 1/1). This gave 4.94 g of the target compound (90% pure, 84% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureunder reflux for 2 h
  4. temperatureThe reaction solution was cooled
  5. customThe solid obtained
  6. filtrationwas filtered off
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-73372e964c0543b0b627fc9fdc4bf173
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Linked notes

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