Butyl chloroformate → 2-Amino-1-n-butoxycarbonyl-4,5-dicyanoimidazole

HRID 1576950Notes

Reaction equation

HRID 1576950 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:9]#[N:10])=[C:5]([C:7]#[N:8])[N:6]=1.C(=O)(O)[O-].[Na+].Cl[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18]>CC(C)=O>[NH2:1][C:2]1[N:3]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[C:4]([C:9]#[N:10])=[C:5]([C:7]#[N:8])[N:6]=1

Participants

5

Reactant 3

HCID 61140Butyl chloroformateHCID 1704461H-Imidazole-4,5-dicarbonitrile, 2-amino-HCID 516892Sodium Bicarbonate

Product 1

HCID 102202732-Amino-1-n-butoxycarbonyl-4,5-dicyanoimidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 g of 2-amino-4,5-dicyanoimidazole was dissolved in 20 ml of suspension of acetone containing 1.3 g of sodium bicarbonate and then 2.1 g of n-butyl chloroformate was added dropwise to said solution at a room temperature. The resulting solution was refluxed during 30 minutes, and white crystal was separated out when the rection mixture was poured into ice-water. After recrystallizing the crude product from methanol, 2.7 g of the purified compound having a melting point of 170° to 172°C was obtained as needles (Yield rate: 77%).

Workup

  1. customat a room temperature
  2. temperatureThe resulting solution was refluxed during 30 minutes
  3. customwhite crystal was separated out when the rection mixture
  4. additionwas poured into ice-water
  5. customAfter recrystallizing the crude product from methanol, 2.7 g of the purified compound
  6. customwas obtained as needles (Yield rate: 77%)

Sources & evidence

ORD record
ord-74a95b4112994c06a0bccf0a4f944f1f
Source dataset
uspto-grants-1976_09
Patent number
US03983241

Reaction notes

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