6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → HCID 67222622, compound

HRID 1801451Notes

Reaction equation

HRID 1801451 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.[C:13]([Si:17]([CH3:25])([CH3:24])[O:18][CH2:19][CH2:20][C@@H:21]1[CH2:23][O:22]1)([CH3:16])([CH3:15])[CH3:14]>CCO.O>[C:13]([Si:17]([CH3:25])([CH3:24])[O:18][CH2:19][CH2:20][C@@H:21]([OH:22])[CH2:23][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)([CH3:14])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 11217932HCID 11217932, compound

Product 1

HCID 67222622HCID 67222622, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 6-amino-4H-benzo[1,4]thiazin-3-one (10.68 g, 59.3 mmol; commercial) and tert-butyl-dimethyl-((R)-2-oxiranyl-ethoxy)-silane (as described in H.i, 12.0 g, 59.3 mmol) in 9-1 EtOH/H2O (320 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure. Residual starting aniline could be removed by addition of ether/MeOH followed by filtration. The mother liquor containing the product was concentrated under reduced pressure to afford the title intermediate as a brown oil (18.8 g, 83% 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 ether/MeOH
  3. filtrationfollowed by filtration
  4. additionThe mother liquor containing the product
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-88362eecc8054047b6b8630af1a0b36f
Source dataset
uspto-grants-2013_01
Patent number
US08349826B2

Reaction notes

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