Sodium Acetate → 7-fluoro-6-trifluoroacetylmethylidenhydrazino-4-propargyl-2H-1,4-benzoxazin-3-one

HRID 48481

Reaction equation

HRID 48481 reaction equation
C([O-])(=O)C.[Na+].Br[CH:7](Br)[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].[F:15][C:16]1[C:29]([NH:30][NH2:31])=[CH:28][C:19]2[N:20]([CH2:25][C:26]#[CH:27])[C:21](=[O:24])[CH2:22][O:23][C:18]=2[CH:17]=1>O>[F:15][C:16]1[C:29]([NH:30][N:31]=[CH:7][C:8](=[O:9])[C:10]([F:13])([F:12])[F:11])=[CH:28][C:19]2[N:20]([CH2:25][C:26]#[CH:27])[C:21](=[O:24])[CH2:22][O:23][C:18]=2[CH:17]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetoneHCID 145179487-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one

Product 1

HCID 739799877-fluoro-6-trifluoroacetylmethylidenhydrazino-4-propargyl-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 8.0 g (97.2 mmol) of sodium acetate and 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 30 minutes. Then, the reaction mixture was cooled to 0° C., to which 4.4 g (18.7 mmol) of 7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water, and dried, which afforded 6.3 g (18.37 mmol) of 7-fluoro-6-trifluoroacetylmethylidenhydrazino-4-propargyl-2H-1,4-benzoxazin-3-one [another name: 3,3,3-trifluoro-2-oxopropanal 1-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-ylhydrazone)], m.p. 190.6° C. (decomp.).

Workup

  1. additionwas added
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed twice with 10 ml of water
  4. customdried

Sources & evidence

ORD record
ord-872b4fd3d1974b1995f81527e7393860
Source dataset
uspto-grants-2004_03
Patent number
US06703503B2

Linked notes

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