Methyl Isocyanate → HCID 13228828, compound

HRID 1648767Notes

Reaction equation

HRID 1648767 reaction equation
[CH3:1][C:2]([NH:5][C:6]([O:8][NH:9][C:10](=[O:12])[CH3:11])=[O:7])([CH3:4])[CH3:3].[CH3:13][N:14]=[C:15]=[O:16]>C(N(CC)CC)C.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:13][NH:14][C:15]([N:9]([O:8][C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:10](=[O:12])[CH3:11])=[O:16]

Participants

6

Reactant 2

HCID 12228Methyl IsocyanateHCID 20481766N-[(tert-Butylcarbamoyl)oxy]acetamide

Product 1

HCID 13228828HCID 13228828, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

N-((((1,1-dimethylethyl)amino)carbonyl)oxy)acetamide (8.7 grams), methyl isocyanate (3.2 grams), and a few drops of triethylamine were stirred at room temperature in 150 ml of methylene chloride for about 12 hours. The solvent was then removed under vacuum leaving an oily residue which was dissolved in hot toluene. Upon cooling, a white crystalline material separated and was collected by filtration. The white crystals were recrystallized from toluene leaving a residue which was mixed with about 50 ml of water for two hours. This mixture was then filtered, and the insoluble material was dried in a vacuum leaving the desired N-((methylamino)carbonyl)-N-((((1,1-dimethylethyl)amino)carbonyl)oxy)acetamide, m.p. 142°-144° C.

Workup

  1. customThe solvent was then removed under vacuum
  2. customleaving an oily residue which
  3. temperatureUpon cooling
  4. customa white crystalline material separated
  5. filtrationwas collected by filtration
  6. customThe white crystals were recrystallized from toluene leaving a residue which
  7. additionwas mixed with about 50 ml of water for two hours
  8. filtrationThis mixture was then filtered
  9. customthe insoluble material was dried in a vacuum

Sources & evidence

ORD record
ord-39e77a7b7dc4407288e3b7a38323af71
Source dataset
uspto-grants-1983_11
Patent number
US04413009

Reaction notes

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