Acetic Anhydride → HCID 13934978, compound

HRID 2308904Notes

Reaction equation

HRID 2308904 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=[CH:12][C:11]=1[CH2:18][N:19]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[CH2:21][O:20]1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl.C(OCC)(=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH:17][C:27]([CH3:28])=[O:29])=[CH:12][C:11]=1[CH2:18][N:19]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[CH2:21][O:20]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13934984HCID 13934984, compound

Product 1

HCID 13934978HCID 13934978, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.6 g, 0.0055 mole) was added to a stirred solution of 2-[(2-chloro-5-hydrazinophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone hydrochloride (1.5 g, 0.005 mole) in methylene chloride (50 ml), followed by the dropwise addition of acetic anhydride (0.6 g, 0.0055 mole). Upon completion of addition, the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with water (3×50 ml). The dried (magnesium sulfate) organic layer was concentrated under reduced pressure. The residue was recrystallized from ethanol-water to yield 0.95 g of 2-[[2-chloro-5-(methylcarbonylhydrazo)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone as a yellow solid; m.p. 178°-180° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. washwashed with water (3×50 ml)
  3. dry with materialThe dried (magnesium sulfate) organic layer
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-c5a75e1f7870445a8800e04a31564f72
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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