6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → HCID 67131227, compound

HRID 1890433Notes

Reaction equation

HRID 1890433 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[CH2:13]([C@@H:15]1[O:17][CH2:16]1)[Cl:14]>CCO.O>[Cl:14][CH2:13][C@H:15]([OH:17])[CH2:16][NH:1][C:2]1[CH:3]=[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 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 67131227HCID 67131227, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 6-amino-4H-benzo[1,4]thiazin-3-one (18.39 g, 102 mmol; commercial) and (R)-epichlorohydrin (8.0 mL, 1 eq.) in 9-1 EtOH/H2O (450 mL) was heated at 80° C. overnight. The mixture was concentrated under reduced pressure. Residual starting aniline could be removed by addition of Et2O/EA followed by filtration. The filtrate containing the product was concentrated under reduced pressure to afford the title intermediate as a beige solid (22.52 g, 81% yield) which was used as such in the next step.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customcould be removed by addition of Et2O/EA
  3. filtrationfollowed by filtration
  4. additionThe filtrate containing the product
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e70cf26dd9b64de8950aaedd4232cc02
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

Loading…