Trifluoroacetic acid → 1H-2,1-Benzothiazine 2,2-dioxide

HRID 1776177Notes

Reaction equation

HRID 1776177 reaction equation
COC1C=CC(C[N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]=[CH:10][S:9]2(=[O:19])=[O:18])=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][S:9]1(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59761315HCID 59761315, compound

Product 1

HCID 218161521H-2,1-Benzothiazine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized according to the method described in WO 2008/073956 A2. To a solution of 1-(4-methoxybenzyl)-1H-benzo[c][1,2]thiazine 2,2-dioxide (0.9 g, 3 mmol) in anhydrous methylene chloride was added trifluoroacetic acid (18 mL). The mixture was stirred at room temperature for 5 hours and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (25-70% ethyl acetate in hexanes) to give a white solid. (0.6 g, 72%). 1H NMR (CDCl3, 300 MHz) δ 7.43-7.38 (m, 2H), 7.29 (m, 1H), 7.20-7.14 (dt, 1H, J=1.2, 7.5 Hz), 7.02-6.99 (d, 1H, J=7.8 Hz), 6.78-6.75 (dd, 1H, J=2.4, 10.5 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by silica gel column chromatography (25-70% ethyl acetate in hexanes)
  3. customto give a white solid

Sources & evidence

ORD record
ord-f93bf75565574038bb5a164adebd0463
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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