1,3,5-Trioxane → 6-Nitro-3,4(1H)-dihydro-2,3-benzothiazine 2,2-dioxide

HRID 522679노트

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HRID 522679 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]1OCOCO1.FC(F)(F)S(O)(=O)=O.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCCl.ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:10][S:11](=[O:12])(=[O:13])[NH:14][CH2:15][C:8]=2[CH:9]=1)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 80811,3,5-TrioxaneHCID 62406Trifluoromethanesulfonic acidHCID 67749Trifluoromethanesulfonic anhydrideHCID 2755281(4-Nitrophenyl)methanesulfonamide

생성물 1

HCID 5959576-Nitro-3,4(1H)-dihydro-2,3-benzothiazine 2,2-dioxide수율 23%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

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온도
35 °C

실험 절차

To a mixture of (4-nitrophenyl)methanesulfonamide (864 mg, 4.0 mmol) and s-trioxane (120 mg, 4.0 mmol) in 1,2-dichoroethane (10 mL) was added trifluoromethanesulfonic acid (1.5 mL), followed by the addition of trifluoromethanesulfonic anhydride (1.5 mL, 4.0 mmol). The reaction mixture was stirred at 35° C. for 2 hours and refluxed overnight. The mixture was then diluted with dichloromethane (100 mL) and washed with water (100 mL) and brine (50 mL). The solvents were evaporated and the residue was purified by Prep-HPLC to give 6-nitro-3,4-dihydro-1H-benzo[d][1,2]thiazine 2,2-dioxide (210 mg, 23%) as a gray solid. MS (ES+) C8H8N2O4S requires: 228, found: 229 [M+H]+.

후처리

  1. temperaturerefluxed overnight
  2. washwashed with water (100 mL) and brine (50 mL)
  3. customThe solvents were evaporated
  4. customthe residue was purified by Prep-HPLC

출처 및 근거

ORD 기록
ord-04ed11a5cc7b4f0082559b7cfe67718d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334263B2

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