4-Toluenesulfonyl chloride → HCID 21866687, compound

HRID 1796381Notes

Reaction equation

HRID 1796381 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-e6f8090963f545b5a26f959de16f88a2
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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