3-Chloropropionyl chloride → 1-(6-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one

HRID 2224071Notes

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.C(=O)(O)[O-].[Na+].[Cl:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>C(OCC)(=O)C>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][CH2:16][N:15]([C:28](=[O:29])[CH2:27][CH2:26][Cl:25])[C:14]=3[CH:19]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.530 g, 1.90 mmol) in 5 mL ethyl acetate was added 2 mL saturated aqueous sodium bicarbonate. The mixture was stirred rapidly and cooled to 0° C., and 3-chloro-propionyl chloride (0.219 mL, 2.30 mmol) was added dropwise over 2 minutes. Stirring was continued for 20 minutes, and 20 mL ethyl acetate was added to the reaction mixture. The organic phase was separated, dried over Na2SO4 and concentrated in vacuo to give 0.689 g (99%) of 1-(6-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-chloro-propan-1-one as an orange-white solid. MS: 367 (M+H)+.

Workup

stirringStirring
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8ba41c80ac93433d9da6ce6ad919d8e8
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378415B2

Reaction notes

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