Dichloromethane → (6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrile

HRID 2224065Notes

Reaction equation

HRID 2224065 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][NH:15][C:14]=3[CH:19]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][C:22]#[N:23].C(N(CC)C(C)C)(C)C.ClCCl>C(Cl)(Cl)Cl.O>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]#[N:23])[C:14]=3[CH:19]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 58641530HCID 58641530, compound

Product 1

HCID 58641518(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 6-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.200 g., 0.727 mmol) in 0.5 mL chloroform was added bromoacetonitrile (0.100 mL, 1.45 mmol) and N,N-diisopropyl ethylamine (0.190 mL, 1.1 mmol). The solution was refluxed for 18 hours and cooled to room temperature. To the reaction mixture was added 15 mL dichloromethane and 20 mL water. The fractions were separated, and the organic fraction was washed with 50 mL water. The organic fraction was dried over Na2SO4, concentrated in vacuo, and the residue purified by flash chromatography (10-50% ethyl acetate in hexanes) to give 0.246 g (0.719 mmol, 99%) of (6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrile as a clear oil. MS: 315 (M+H)+.

Workup

  1. temperatureThe solution was refluxed for 18 hours
  2. customThe fractions were separated
  3. washthe organic fraction was washed with 50 mL water
  4. dry with materialThe organic fraction was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by flash chromatography (10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-30699179465644c6844273b5d5f2fad4
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

Loading…