Morpholine → 5-Methylsulfanyl-2-morpholin-4-yl-benzoic acid

HRID 736192ノート

反応式

HRID 736192 の反応式
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCCC.[Cu]>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

参加物

6

反応物 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

生成物 1

HCID 597935765-Methylsulfanyl-2-morpholin-4-yl-benzoic acid収率 10.1%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 62761-Pentanol溶媒

実験手順

A mixture of 2-Chloro-5-(methylthio)-benzoic acid (1 g, 4.7 mmol), morpholine (620 ul, 7.1 mmol), potassium carbonate (1.05 g, 7.6 mmol) and Copper (24 mg, 0.38 mmol) in pentanol (6 ml) was stirred for 1 h at room temperature. The mixture was heated to 100° C. and stirred for 40 minutes. The solvent was evaporated. The residue was taken up in water and acidified to pH 2. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate 0-20% over 15 minutes to provide the title compound as a brown solid (120 mg, 10%), MS (m/e): 252.1 (M−H, 100%)

後処理

  1. temperatureThe mixture was heated to 100° C.
  2. stirringstirred for 40 minutes
  3. customThe solvent was evaporated
  4. extractionThe aqueous layer was extracted twice with ethylacetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude oil was chromatographed over silicagel

出典と根拠

ORDレコード
ord-cc8f0abe003647f3bf02ecc0ce8cdb3b
出典データセット
uspto-grants-2009_09
特許番号
US07595314B2

反応ノート

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