[(2,4-Dinitrophenyl)thio]acetic acid → 6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one

HRID 74053

반응식

HRID 74053 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[S:13][CH2:14][C:15]([OH:17])=O)([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]2[S:13][CH2:14][C:15](=[O:17])[NH:1][C:4]=2[CH:9]=1

참가 물질

4

반응물 2

HCID 60055[(2,4-Dinitrophenyl)thio]acetic acidHCID 61436Stannous chloride dihydrate

생성물 1

HCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one수율 61.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-(2,4-dinitrophenylthio)-acetic acid (2.3 g, 9 mmol) and tin (II) chloride dihydrate (22.6 g, 0.1 mol) in ethanol (30 mL) was refluxed overnight. After removal of the solvent under reduced pressure, the residual slurry was diluted with water (100 mL) and basified with 10% Na2CO3 solution to pH 8. The resulting suspension was extracted with ethyl acetate (3×100 mL). The ethyl acetate extract was washed with water and brine, dried over Na2SO4, and concentrated. The residue was washed with CH2Cl2 to yield 6-amino-2H-benzo[b][1,4]thiazin-3(4H)-one (DC-7) as a yellow powder (1 g, 52%). 1H NMR (DMSO-d6) δ 10.24 (s, 1H), 6.88 (d, 1H, J=6 Hz), 6.19-6.21 (m, 2H), 5.15 (s, 2H), 3.28 (s, 2H); ESI-MS 181.1 m/z (MH+).

후처리

  1. customAfter removal of the solvent under reduced pressure
  2. additionthe residual slurry was diluted with water (100 mL)
  3. extractionThe resulting suspension was extracted with ethyl acetate (3×100 mL)
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. washThe residue was washed with CH2Cl2

출처 및 근거

ORD 기록
ord-db606a9c235d4eb6b0c36ff0c178f2f5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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