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

HRID 1457326

반응식

HRID 1457326 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 221044663-(2-Benzoylbenzoyl)-4-thiazolidinemethanol수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-21cea4eb360c472eb84462b7a0d7079c
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05847155

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