Isobutyl chloroformate → HCID 54067442, compound

HRID 1283756Notes

Reaction equation

HRID 1283756 reaction equation
[Na].[OH:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14].C(=O)([O-])O.[Na+]>O.CC(C)=O>[CH2:16]([O:15][C:13]([O:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:14])[CH:17]([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 54067442HCID 54067442, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of sodium salt of ethyl 2-hydroxyimino-2-cyanoacetate (16.4 g) in water (100 ml), isobutyl chloroformate (13.7 g) and acetone (10 ml) are added, and the resulting mixture is stirred at a temperature lower than 20°C. After adjusting pH to 7 with the addition of an aqueous solution of sodium hydrogencarbonate, stirring is continued for 3 hours. The reaction mixture is extracted with ethyl acetate, and the organic layer is washed with water, dried and concentrated. The residue is crystallized with the addition of petroleum ether and collected by filtration. Recrystallization from petroleum ether containing a small amount of ethyl acetate affords ethyl 2-isobutoxycarbonyloxyimino-2-cyanoacetate (14.1 g) as scales. M.P. 60 to 62°C.

Workup

  1. stirringstirring
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. washthe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is crystallized with the addition of petroleum ether
  7. filtrationcollected by filtration
  8. customRecrystallization from petroleum ether containing a small amount of ethyl acetate

Sources & evidence

ORD record
ord-fe1bd1e5c0f1491eadbc1dc62717b715
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

Loading…