4-Toluenesulfonyl chloride → HCID 21866687, compound

HRID 890655Notes

Reaction equation

HRID 890655 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]([C:16]([F:19])([F:18])[F:17])=[C:10]([CH2:12][CH2:13][CH2:14][OH:15])[N:11]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([O:15][CH2:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:20])=[CH:2][CH:3]=3)[O:8][C:9]=2[C:16]([F:18])([F:19])[F:17])(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21866935HCID 21866935, compound

Product 1

HCID 21866687HCID 21866687, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-[2-(p-Tolyl)-5-trifluoromethyloxazol-4-yl]-1-propanol (6.40 g) synthesized according to the method of Kawase et. al. (Chem. Pharm. Bull., 46, 749–756(1998)) was dissolved in 35 ml of dichloromethane. To the solution were added sequentially 293 mg of 4-(dimethylamino)pyridine, 4.7 ml of triethylamine and 5.13 g of p-toluenesulfonyl chloride, and stirred for 3 hours at room temperature. To the reaction solution was added ethyl acetate, and washed with water, 10% hydrochloric acid and an aqueous solution of saturated aqueous sodium hydrogen carbonate solution sequentially, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide 10.08 g of the objective compound as pale brown crystals. M.p. 57–58° C.

Workup

  1. washwashed with water, 10% hydrochloric acid
  2. dry with materialan aqueous solution of saturated aqueous sodium hydrogen carbonate solution sequentially, and dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2d1dfa1db91b431ba2f2989b18cc2fe9
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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