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

HRID 234909Notes

Reaction equation

HRID 234909 reaction equation
[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:5]=2[O:4]1)[CH3:2].S(Cl)([Cl:22])=O>>[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([Cl:22])=[O:19])=[CH:16][C:5]=2[O:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10515674(S)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid

Product 1

HCID 22869183(S)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride

Procedure

A mixture of (S)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid (0.70 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-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carbonyl chloride (0.70 g).

Workup

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

Sources & evidence

ORD record
ord-fee924d01f6548b583c78f1339d64f38
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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