Acetic Anhydride → HCID 44625727, compound

HRID 1190828Notes

Reaction equation

HRID 1190828 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[OH:12][C:13]1[C:20]([Br:21])=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[Br:22].[C:23](OC(=O)C)(=[O:25])[CH3:24].C(N(CC)CC)C>>[C:23]([O:12][C:13]1[C:20]([Br:21])=[CH:19][C:16](/[CH:17]=[C:2]2/[C:3](=[O:11])[NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:1]/2)=[CH:15][C:14]=1[Br:22])(=[O:25])[CH3:24]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 727572H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 44625727HCID 44625727, compound

Procedure

A stirred mixture of (0.5 g, 3.35 mmol) of 2H-1,4-benzoxazin-3(4H)-one, 1.4 g of 4-hydroxy-3,5-dibromo benzaldehyde, 1.68 mL (17.729 mmol) of acetic anhydride and 0.7 mL (5 mmol) of triethyl amine was refluxed for 7 h, left overnight at room temperature and poured into crushed ice. The precipitated solid was collected by filtration and washed with acetonitrile. The crude product was purified by recrystallization from DMF: ethanol.

Workup

  1. temperaturewas refluxed for 7 h
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with acetonitrile
  6. customThe crude product was purified by recrystallization from DMF

Sources & evidence

ORD record
ord-665dd0c1f47f4761a7a26f057421adc4
Source dataset
uspto-grants-2014_03
Patent number
US08680094B2

Reaction notes

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