(+)-Epichlorohydrin → HCID 66954769, compound

HRID 1511807Notes

Reaction equation

HRID 1511807 reaction equation
[NH2:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[CH2:14]([C@H:16]1[O:18][CH2:17]1)[Cl:15]>CCO.O>[Cl:15][CH2:14][CH:16]([OH:18])[CH2:17][NH:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 149428(+)-EpichlorohydrinHCID 66954285HCID 66954285, compound

Product 1

HCID 66954769HCID 66954769, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 6-amino-7-fluoro-4H-benzo[1,4]thiazin-3-one (1 g, 5 mmol, Bioscience, Biotechnology, and Biochemistry 1994, 58, 788) and (S)-epichlorohydrin (0.467 g, 5 mmol) in EtOH/H2O (9:1, 20 mL) was heated at 80° C. for 3 d. The volatiles were removed under reduced pressure and the residue was crystallized from MeOH to give a brown solid (0.83 g, 57%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-7eb5e2eb68e7446ba3520f4f0cce42a7
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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