Acetohydroxamic Acid → 4-Methoxy-1,2-benzoxazol-3-amine

HRID 16396

Reaction equation

HRID 16396 reaction equation
[C:1]([NH:4][OH:5])(=O)[CH3:2].CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19]C=[C:17]([O:21][CH3:22])[C:14]=1C#N.[Cl-].[Na+].C[N:26](C)C=O>>[CH3:22][O:21][C:17]1[C:2]2[C:1]([NH2:26])=[N:4][O:5][C:19]=2[CH:20]=[CH:13][CH:14]=1

Participants

6

Reactant 5

HCID 1990Acetohydroxamic AcidHCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 5231012-Fluoro-6-methoxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 27797514-Methoxy-1,2-benzoxazol-3-amine

Conditions

Temperature
60 °C

Procedure

709.5 mg (9.45 mmol) of acetohydroxamic acid are initially charged in 8 ml of anhydrous dimethylformamide, and 1.06 g (9.45 mmol) of potassium tert-butoxide are added at room temperature. After 40 minutes of stirring, 1 g (6.62 mmol) of 2-fluoro-6-methoxybenzonitrile is added. The mixture is heated at 60° C. for 16 hours. 20 ml of saturated sodium chloride solution are then added to the reaction mixture. The precipitated crystals are filtered off with suction and washed with water.

Workup

  1. filtrationThe precipitated crystals are filtered off with suction
  2. washwashed with water

Sources & evidence

ORD record
ord-acb4e7ee3dec4c4ea677ed50342c344e
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

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