Hexane → HCID 13228808, compound

HRID 1648766Notes

Reaction equation

HRID 1648766 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[C:3]([NH:5][OH:6])=[O:4].[CH3:9][N:10]=[C:11]=[O:12].CCCCCC>C(N(CC)CC)C.C(Cl)Cl>[CH3:9][NH:10][C:11]([N:5]([O:6][C:11]([NH:10][CH3:9])=[O:12])[C:3](=[O:4])[C:2]([CH3:8])([CH3:7])[CH3:1])=[O:12]

Participants

6

Reactant 3

HCID 8058HexaneHCID 12228Methyl IsocyanateHCID 303148N-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 13228808HCID 13228808, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

(2,2-dimethyl)propiohydroxamic acid (5.9 grams), methyl isocyanate (6.5 grams), and a few drops of triethylamine were stirred in about 50 ml of methylene chloride over a period of about 48 hours. This mixture was then concentrated under vacuum leaving a colorless, oily residue. Trituration of this oil with hexane left a sticky solid which was recrystallized from a solution of methylene chloride and hexane. Subsequent recrystallization from a minimal amount of methylene chloride and toluene left the desired, N-((methylamino)carbonyl)-N-((methylamino)carbonyl)oxy)(2,2-dimethyl)propionamide as white crystals, m.p. 117°-119° C. (with slight sintering from about 116° C.).

Workup

  1. concentrationThis mixture was then concentrated under vacuum
  2. customleaving a colorless, oily residue
  3. customwas recrystallized from a solution of methylene chloride and hexane
  4. customSubsequent recrystallization from a minimal amount of methylene chloride and toluene
  5. waitleft the
  6. custom(2,2-dimethyl)propionamide as white crystals, m.p. 117°-119° C. (with slight sintering from about 116° C.)

Sources & evidence

ORD record
ord-a6e93e74051044778e4903f9ebdc6901
Source dataset
uspto-grants-1983_11
Patent number
US04413009

Reaction notes

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