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Methanol → Methyl 2-hydroxy-5-sulfamoylbenzoate

HRID 1820822
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HRID 1820822 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1N=CN(C(N2C=NC=C2)=O)C=1.CO>C1COCC1>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:9]=[CH:10][C:2]=1[OH:1]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 77312702-Hydroxy-5-sulfamoylbenzoic acid

생성물 1

HCID 14266941Methyl 2-hydroxy-5-sulfamoylbenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To 62 mmol 2-hydroxy-5-sulfamoyl-benzoic acid in 80 ml THF was added 80 mmol CDI and the mixture heated at 50° C. for 1 h. 616 mmol methanol was then added, and the mixture was heated at 50° C. for 16 h. The mixture was then cooled to room temperature, concentrated in vacuo, and the residue chromatographed on silica gel (eluant: dichloromethane/methanol 20:1). The product containing fractions were concentrated in vacuo and the residue suspended in ethyl acetate and washed with aq NaHCO3 solution. The organic phase was dried with Na2SO4 and concentrated in vacuo to afford the title compound. MS (m/e): 230.2 ([M−H]−, 100%)

후처리

  1. temperaturethe mixture was heated at 50° C. for 16 h
  2. temperatureThe mixture was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customthe residue chromatographed on silica gel (eluant: dichloromethane/methanol 20:1)
  5. additionThe product containing fractions
  6. concentrationwere concentrated in vacuo
  7. washwashed with aq NaHCO3 solution
  8. dry with materialThe organic phase was dried with Na2SO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-60b045a39ba14cd9aa06ad504ff2a7d7
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07605163B2

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