Carbon Dioxide → 2-Hydroxybenzenecarbothioamide

HRID 260024

反応式

HRID 260024 の反応式
[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]

参加物

9

反応物 5

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 9274O,O-Diethyl dithiophosphateHCID 119072-HydroxybenzonitrileHCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 27593422-Hydroxybenzenecarbothioamide収率 55%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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 1H NMR data as reported in the literature (Yousif, N. M. Tetrahedron 1989, 45, 4599).

後処理

  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%)

出典と根拠

ORDレコード
ord-06794c3600924e5990f6517c2d22683c
出典データセット
uspto-grants-1996_06
特許番号
US05525599

関連ノート

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