Carbon Dioxide → 2-Hydroxybenzenecarbothioamide

HRID 53573

반응식

HRID 53573 반응식
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].P(S)(OCC)(OCC)=[S:11].C([O-])(O)=O.[Na+].C(=O)=O.[Na+].[Cl-]>C(Cl)Cl.CCOCC.O>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[S:11])[NH2:5]

참가 물질

9

반응물 5

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 9274O,O-Diethyl dithiophosphateHCID 119072-HydroxybenzonitrileHCID 516892Sodium Bicarbonate2회

생성물 1

HCID 27593422-Hydroxybenzenecarbothioamide수율 55%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A stirred solution of 2-hydroxybenzonitrile (23.8 g, 200 mmol), (EtO)2P(S)SH (33.6 mL, 200 mmol) and water (40 mL) was heated at 80° C. for 12 hr under nitrogen. The mixture was cooled down to 0°-10° C., diluted with CH2Cl2 (200 mL)/Et2O (400 mL), then cautiously treated with saturated aq. NaHCO3 (60 mL), and followed by adding solid NaHCO3 in small portions until CO2 evolution ceased. Half-saturated aq. NaCl (40 mL) was added to the mixture. The organic layer was separated, washed with brine (100 mL), dried over MgSO4, and filtered. After concentration in vacuo, the residue was chromatographed on silica gel (gradient EtOAc/CH2Cl2 :0-5%) to give 3a (16.7 g, 55%) as a pinkish solid, which had the same 1HNMR data as reported in the literature (Yousif, N. M. Tetrahedron 1989, 45, 4599).

후처리

  1. temperatureThe mixture was cooled down to 0°-10° C.
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationAfter concentration in vacuo
  7. customthe residue was chromatographed on silica gel (gradient EtOAc/CH2Cl2 :0-5%)

출처 및 근거

ORD 기록
ord-a726745185ea4e27ab755f57b036fc7d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620968

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