Acetic Anhydride → HCID 67517093, compound

HRID 1754327Notes

Reaction equation

HRID 1754327 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:5]([NH:7][N:8]=[C:9]([CH3:11])[CH3:10])=[O:6].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:9]([CH3:11])([CH3:10])[N:8]([C:16](=[O:18])[CH3:17])[N:7]=2)[CH:12]=[CH:13][C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 922186HCID 922186, compound

Product 1

HCID 67517093HCID 67517093, compound

Procedure

A mixture of 3-bromo-4-methyl-N′-(propan-2-ylidene)benzohydrazide (2.0 g, 7.46 mmol), as obtained hereinbefore, and acetic anhydride (30 mL) was refluxed for one hour. The excess of acetic anhydride was removed under vacuum after cooling the reaction mixture to room temperature and the crude residue obtained was triturated with hexane to remove traces of acetic anhydride present in the reaction mixture. The crude product was purified by flash column chromatography (silica gel, 100-200 mesh, 13% ethyl acetate in hexane) to afford 800 mg of the desired product as an oil. 1HNMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 2.44 (s, 3H), 2.29 (s, 3H), 1.85 (s, 6H); ESI-MS (m/z) 311, 313 [(MH)+, Br79,81].

Workup

  1. customas obtained hereinbefore
  2. customThe excess of acetic anhydride was removed under vacuum
  3. customthe crude residue obtained
  4. customwas triturated with hexane
  5. customto remove traces of acetic anhydride present in the reaction mixture
  6. customThe crude product was purified by flash column chromatography (silica gel, 100-200 mesh, 13% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-62aaa53da132495897af8fdd04f1ee2a
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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