n-Butyl carbamate → Butyloxycarbonyl isocyanate

HRID 1283794Notes

Reaction equation

HRID 1283794 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[C:7](=[O:14])([O:9][CH2:10][CH2:11][CH2:12][CH3:13])[NH2:8]>C(Cl)(Cl)Cl>[CH2:10]([O:9][C:7]([N:8]=[C:2]=[O:3])=[O:14])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 11596n-Butyl carbamateHCID 65578Oxalyl chloride

Product 1

HCID 12538171Butyloxycarbonyl isocyanate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Oxalyl chloride (25.0 g., 0.2 mol.) is added to a suspension of 16.4 g. (0.14 mol.) of butyl carbamate in 75 ml. of chloroform. After cessation of gas evolution, the reaction mixture is refluxed in a nitrogen atmosphere for 12 hours. The mixture is cooled, filtered and the filtrate is distilled in vacuo to give butoxycarbonyl isocyanate.

Workup

  1. temperatureAfter cessation of gas evolution, the reaction mixture is refluxed in a nitrogen atmosphere for 12 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. distillationthe filtrate is distilled in vacuo

Sources & evidence

ORD record
ord-a1da8fd0e9704ea4a29453683ae76504
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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