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

HRID 522679ノート

反応式

HRID 522679 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-04ed11a5cc7b4f0082559b7cfe67718d
出典データセット
uspto-grants-2016_05
特許番号
US09334263B2

反応ノート

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