Acetic Anhydride → HCID 86744037, compound

HRID 2107852Notes

Reaction equation

HRID 2107852 reaction equation
[CH:1]([C:3]1[NH:4][C:5]([CH3:34])=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[CH:20]=[CH:21]/[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.Cl.[NH2:36]O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([C:3]1[NH:4][C:5]([CH3:34])=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[CH:20]=[CH:21]/[C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:36]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86744036HCID 86744036, compound

Product 1

HCID 86744037HCID 86744037, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 2 (2.9 g), hydroxylamine hydrochloride (0.51 g) and sodium acetate (0.76 g) in acetic acid (30 ml) was stirred for 2 h at room temperature, then acetic anhydride (2.2 g) was added to the reaction. The mixture was heated to 95°-100° for 5 h and then extracted with ethyl acetate. The organic phase was washed with 5% sodium hydroxide and brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with cyclohexane/ethyl acetate 7:3 to give the title compound (0.45 g) as a yellow solid. M.p. 146°-147°.

Workup

  1. temperatureThe mixture was heated to 95°-100° for 5 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 5% sodium hydroxide and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with cyclohexane/ethyl acetate 7:3

Sources & evidence

ORD record
ord-dabf19ed22bd4b5887394ee5d8c24efb
Source dataset
uspto-grants-1990_06
Patent number
US04935548

Reaction notes

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