N-bromobutanimide → 6-Bromoacetyl-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

HRID 17395Notes

Reaction equation

HRID 17395 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]([O:28]CC)=[CH2:27])[C:12]=1[CH3:31])#[N:10]>O1CCCC1.O>[Br:1][CH2:28][C:26]([C:13]1[C:12]([CH3:31])=[C:11]([C:9]#[N:10])[C:16]2[N:17]=[C:18]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[O:19][C:15]=2[C:14]=1[F:25])=[O:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 685850534-cyano-6-[1-(ethoxy)ethenyl]-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

Product 1

HCID 866308456-Bromoacetyl-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Next, at room temperature, N-bromosuccinimide (2.10 g, 11.8 mmol) was added to a tetrahydrofuran/water (178 ml/11 ml) mixed solution of the obtained 4-cyano-6-[1-(ethoxy)ethenyl]-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide (3.56 g, 11.2 mmol), and stirred for 20 minutes. The solvent was evaporated away under reduced pressure, and the resulting residue was dissolved in ethyl acetate, and the solution was washed with water.

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washthe solution was washed with water

Sources & evidence

ORD record
ord-3326e4a266eb4e70b9accc45988aa27d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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