1,2-Dichloroethane → 161190-38-1

HRID 1736409Notes

Reaction equation

HRID 1736409 reaction equation
ClCCCl.[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])[CH2:26][CH2:25]2.[O-:33]O.C1(C(C)C)C=CC=CC=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S@:17]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])[CH2:26][CH2:25]2)=[O:33]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 10668289HCID 10668289, compoundHCID 53627471Cumen hydroperoxide

Product 1

HCID 9866215161190-38-1Yield 3.2%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

To 1 l of 1,2-dichloroethane were added 56.8 g of titanium tetraisopropoxide, 168 g of D-(-)-diethyl tartarate, 0.91 ml of water and 80 g of 6-{3-[1-(2-methylphenyl)-2-imidazolylthio]propoxy}-3,4-dihydrocarbostyril. The mixture was stirred and then cooled to -5° C. Thereto was added 124 g of cumene hydroperoxide slowly. After the completion of the addition, the mixture was stirred at 5° C. for 18 hours. The reaction was repeated. The reaction mixtures from the two reactions were combined and purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=3/1/0→30/10/1), followed by recrystallization from ethanol-ethyl acetate. The mother liquor was concentrated to obtain crystals. This procedure was conducted 14 times. The resulting crystals were purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1), followed by recrystallization from ethanol to obtain 2.7 g of (S)-(+)-6-{3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]propoxy}-3,4-dihydrocarbostyril. White powder.

Workup

  1. additionAfter the completion of the addition
  2. stirringthe mixture was stirred at 5° C. for 18 hours
  3. custompurified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=3/1/0→30/10/1)
  4. customfollowed by recrystallization from ethanol-ethyl acetate
  5. concentrationThe mother liquor was concentrated
  6. customto obtain crystals
  7. customThe resulting crystals were purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1)
  8. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-7f2171dc27c749a5acd016514f343fd8
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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