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

HRID 376983Notes

Reaction equation

HRID 376983 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-44b9701d98794277954c24870002d79a
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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