4-Toluenesulfonyl chloride → HCID 86741463, compound

HRID 569584Notes

Reaction equation

HRID 569584 reaction equation
ClC1C=C(Cl)C=CC=1N1CCN=C1[CH:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CCN1C=CN=C1.[N:28]1([CH2:33][CH2:34][OH:35])[CH:32]=[CH:31][N:30]=[CH:29]1.C(N(CC)CC)C.C1(C)C=CC([S:49](Cl)(=[O:51])=[O:50])=CC=1>ClCCl>[N:28]1([CH2:33][CH2:34][O:35][S:49]([C:27]2[C:22]([CH3:14])=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:51])=[O:50])[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 20147694HCID 20147694, compound

Product 1

HCID 86741463HCID 86741463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

1-(2,4-Dichlorophenyl)-4,5-dihydro-2-[3-(imidazol-1-yl)-1-phenylpropyl]imidazole To a stirred solution of 2-(imidazol-1-yl)ethanol (1.9 g, 0.0156 mol), triethylamine (2.8 ml, 0.0187 mol), and 4-N,N-dimethylaminopyridine (20 mg) in dichloromethane (20 ml) at a temperature of -78° C. under nitrogen atmosphere, was added p-toluenesulphonyl chloride (3.6 g, 0.0187 mol) in dichloromethane (10 ml). The reaction mixture was allowed to warm to -10° C. and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. The organic phase was separated and the aqueous phase extracted with dichloromethane. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield colorless crystals of 2-(imidazol-1-yl)-1-toluenesulphonyloxyethane (4.23 g). n-Butyllithium (3.9 ml, 0.0059 mol, 1.5M in hexane) was added to a stirred solution of 1-(2,4-dichlorophenyl)-4,5-dihydro-2-phenylmethylimidazole (1.5 g, 0.0049 mol) in dry tetrahydrofuran (10 ml) at -78° C. under a nitrogen atmosphere. Copper(I)bromide-dimethyl sulphide complex (50 mg, 0.0024 mol) was added to the reaction mixture. After a period of one hour, a solution of 2-(imidazol-1-yl)-1-toluenesulphonyloxyethane (2 g, 0.0072 mol) in tetrahydrofuran (7 ml) was added to the reaction mixture. The resulting mixture was allowed to warm to room temperature and allowed to react for 15 hours before being quenched with saturated aqueous ammonium chloride. The phases were separated and the aqueous phase extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield an oil which was chromatographed on silica gel with ammonia/methanol/ethyl acetate (1:4:45) to yield 1-(2,4-dichlorophenyl)-4,5-dihydro-2-[3-(imidazol-1-yl)-1-phenylpropyl]imidazole (1 g) which upon treatment with ethereal hydrogen chloride yielded the hydrochloride salt of 1-(2,4-dichlorophenyl)-4,5-dihydro-2-[3-(imidazol-1-yl)-1-phenylpropyl]imidazole. (Found C, 49.00; H, 5.03; N, 10.76. C21H22N4Cl4.9/4H2O requires C, 49.19; H, 5.21; N, 10.93) having the formula ##STR43##

Workup

  1. customwas then quenched by the addition of saturated aqueous sodium hydrogen carbonate
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b2ff95dbe1f49df885fdc071bd7ead5
Source dataset
uspto-grants-1988_03
Patent number
US04732989

Reaction notes

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