Water → 4-(2-fluorobenzyl)-2H-benzo[b][1,4]thiazin-3(4H)-one

HRID 576500Notes

Reaction equation

HRID 576500 reaction equation
[S:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20].CC([O-])(C)C.[K+].O>CN(C=O)C>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:4]1[C:5](=[O:7])[CH2:6][S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 213964H-1,4-Benzothiazin-3-oneHCID 67968alpha-Bromo-o-fluorotolueneHCID 23665647Potassium tert-butoxide

Product 1

HCID 32444154-(2-fluorobenzyl)-2H-benzo[b][1,4]thiazin-3(4H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2H-benzo[b][1,4]thiazin-3(4H)-one (1.0 g, 6.1 mmole) and 1-(bromomethyl)-2-fluorobenzene (0.76 mL, 1.05 equiv) in DMF (10 mL) was added t-BuOK (0.75 g) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. Water was added and the resulted solid was filtrated, rinsed with water, and dried under vacuum to provide 4-(2-fluorobenzyl)-2H-benzo[b][1,4]thiazin-3(4H)-one (1.51 g, 91%).

Workup

  1. filtrationthe resulted solid was filtrated
  2. washrinsed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f15663c385494b618ea171c6bf5626a6
Source dataset
uspto-grants-2015_05
Patent number
US09040508B2

Reaction notes

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