Chlorosulfonic acid → 4-[2-(4-Methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonyl chloride

HRID 604461Notes

Reaction equation

HRID 604461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.[Cl:22][S:23](O)(=[O:25])=[O:24]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([S:23]([Cl:22])(=[O:25])=[O:24])=[CH:18][CH:17]=3)[N:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 575431862-(4-Methoxy-phenyl)-4-phenoxymethyl-oxazole

Product 1

HCID 575431834-[2-(4-Methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

950 mg 2-(4-Methoxy-phenyl)-4-phenoxymethyl-oxazole were dissolved in 9 ml dichloromethane. At −20° C. 0.90 ml chlorosulfonic acid were added dropwise. The cooling bath was removed and the reaction mixture stirred at room temperature for two hours. The reaction mixture was cooled to 0° C., then 20 ml ice water were added and the reaction mixture extracted five times with portions of 50 ml dichloromethane. The combined organic layers were washed with water and then dried over MgSO4. The solvent was then removed in vacuo to obtain 580 mg 4-[2-(4-Methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonyl chloride.

Workup

  1. customAt −20° C
  2. customThe cooling bath was removed
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. addition20 ml ice water were added
  5. extractionthe reaction mixture extracted five times with portions of 50 ml dichloromethane
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over MgSO4
  8. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-9a8cbb057afc48288e1b8089a87a6783
Source dataset
uspto-grants-2011_03
Patent number
US07910612B2

Reaction notes

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