2-Benzoylbenzoic Acid → 3-(2-Benzoylbenzoyl)-4-thiazolidinemethanol

HRID 1457326

反応式

HRID 1457326 の反応式
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[S:29]1[CH2:33][CH:32]([CH2:34][OH:35])[NH:31][CH2:30]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([N:31]1[CH:32]([CH2:34][OH:35])[CH2:33][S:29][CH2:30]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 68132-Benzoylbenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3213334-ThiazolidinemethanolHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 221044663-(2-Benzoylbenzoyl)-4-thiazolidinemethanol収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.9 g (8.4 mmol) of o-benzoylbenzoic acid and 1.13 g (8.4 mmol) of 1-hydroxybenzotriazole hydrate were combined in 50 ml of methylene chloride and stirred for 20 minutes at room temperature. 1.0 g (8.4 mmol) of 4-thiazolidinemethanol was added, followed by 1.6 g (8.4 mmol) of ethyl-3-(3-dimethylaminopropyl)carbodiimide. The reaction mixture was stirred for 18 hours at room temperature and washed with water, first at pH 2.5 and then at pH 9.5. The organic phase was dried and evaporated to give a foam which was chromatographed on silica gel using 1:1/chloroform:ethyl acetate as the eluant to yield 1.1 g (40%) of the title compound. 1H NMR (CDCl3) δ: 7.4-7.85(m,9H); 4.65(m,1H) ; 4.20-4.40(m,2H); 3.96(m,1H); 3.60-3.70(m,2H); 3.0-3.30(m,2H). High Resolution Mass Spectrum: m/e=328.1015±0.8 ppm (calculated for C18H18NO3S).

後処理

  1. stirringThe reaction mixture was stirred for 18 hours at room temperature
  2. washwashed with water, first at pH 2.5
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give a foam which
  6. customwas chromatographed on silica gel using 1:1/chloroform

出典と根拠

ORDレコード
ord-21cea4eb360c472eb84462b7a0d7079c
出典データセット
uspto-grants-1998_12
特許番号
US05847155

関連ノート

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