Thionyl Chloride → (S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride

HRID 234916Notes

Reaction equation

HRID 234916 reaction equation
[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[C:6]2[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:5]=2[O:4]1)[CH3:2].S(Cl)([Cl:21])=O>>[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[C:6]2[CH:12]=[CH:13][C:14]([C:16]([Cl:21])=[O:18])=[CH:15][C:5]=2[O:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10776998(S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid

Product 1

HCID 53773861(S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride

Procedure

A mixture of (S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid (1.1 g) in thionyl chloride (15 ml) was stirred under reflux for 2 hours. Thionyl chloride was distilled off under reduced pressure to give (S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride (1.25 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationThionyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-856ad682baab4deeb8401e548fcb4743
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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