1,3-Propanedithiol → 1-[4'-(3-Mercapto-propylthio)-biphenyl-4-yl]-2-methyl-2-morpholin-4-yl-propan-1-one

HRID 376983노트

반응식

HRID 376983 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:24])[C:15]([CH3:23])([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CC(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)C.[CH2:60]([SH:64])[CH2:61][CH2:62][SH:63].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.O>[SH:63][CH2:62][CH2:61][CH2:60][S:64][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:24])[C:15]([CH3:23])([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 80131,3-PropanedithiolHCID 11430Potassium CarbonateHCID 92212Bisphenol A diglycidyl ether diacrylateHCID 193606221-(4'-Bromo-biphenyl-4-yl)-2-methyl-2-morpholin-4-yl-propan-1-one

생성물 1

HCID 193605971-[4'-(3-Mercapto-propylthio)-biphenyl-4-yl]-2-methyl-2-morpholin-4-yl-propan-1-one

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

3.5 g (9.0 mmol) of 1-(4'-Bromo-biphenyl-4-yl)-2-methyl-2-morpholin-4-yl-propan-1-one (prepared by the method described in EP-A-3002) and 5.4 ml (54 mmol) of 1,3-propanedithiol are dissolved in 50 ml of dimethylacetamide, and the solution is stirred at around 140° C. together with 2.5 g of potassium carbonate for 2.5 h. Then the solution is cooled to room temperature and poured into water. The crude product is extracted with methylene chloride, washed with saturated sodium chloride solution, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (10:90) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.35 (s, 6H), 1.38 (t, 1H), 1.98 (tt, 2H), 2.61 (t, 4H), 2.69 (dt, 2H), 3.11 (t, 2H), 3.72 (t, 4H), 7.42 (d, 2H), 7.51 (d, 2H), 7.62 (d, 2H), 8.63 (d, 2H).

후처리

  1. extractionThe crude product is extracted with methylene chloride
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (10:90) as an eluent

출처 및 근거

ORD 기록
ord-44b9701d98794277954c24870002d79a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022906

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