Hydrochloric Acid → 6-mercapto-2H-1,4-benzoxazin-3(4H)-one

HRID 1192257노트

반응식

HRID 1192257 반응식
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([S:12](Cl)(=O)=O)=[CH:11][C:4]=2[NH:3]1.Cl.[Sn].C(OCC)(=O)C>O1CCOCC1>[SH:12][C:10]1[CH:9]=[CH:8][C:5]2[O:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=2[CH:11]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 52002293-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-sulfonyl chlorideHCID 5352426Tin atom

생성물 1

HCID 162277896-mercapto-2H-1,4-benzoxazin-3(4H)-one수율 16.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonyl chloride (5.8 g, 20.2 mmol), was added the hydrogen chloride in 1,4-dioxane (30 mL) followed by tin powder (12 g, 10.1 mmol). The resulting mixture was heated under reflux for 2 hours. After this time, the solvent of the reaction mixture was removed under vacuum to give the crude residue. The resulting residue was treated with ethyl acetate and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography using a 60:40 mixture of hexane and ethyl acetate as eluent to afford the title product as a white solid (0.59 g, 16% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.82 (1H, s), 6.86 (2H, m), 6.81 (1H, m), 5.40 (1H, s), 4.53 (2H, s).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter this time, the solvent of the reaction mixture was removed under vacuum
  4. customto give the crude residue
  5. washwashed with brine and water
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography
  10. additiona 60:40 mixture of hexane and ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-f92917e49b9b4f7392d5cfea292906fd
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680139B2

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