Water → HCID 19966303, compound

HRID 977849Notes

Reaction equation

HRID 977849 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2:6](N(CC)CC)C.C(Cl)Cl.O[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH3:25])[C:19]=1[N+:26]([O-:28])=[O:27].[OH2:29]>>[S:1]([O:3][CH2:6][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH3:25])[C:19]=1[N+:26]([O-:28])=[O:27])([CH3:4])(=[O:2])=[O:29]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19966258HCID 19966258, compound

Product 1

HCID 19966303HCID 19966303, compound

Procedure

76 mg (0.66 mmol) of mesyl chloride and then 69 mg (0.68 mmol) of triethylamine were added to 5 ml of a methylene chloride solution containing 100 mg (0.50 mmol) of 2-hydroxymethyl-6-methylthio-1-nitrobenzene, in an ice bath. The mixture was stirred at the temperature of the ice bath for 1 hour and 15 minutes. At the end of this time, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic extract was separated and washed with 2N aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure, to obtain the title compound. This product was used for the next step without purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with 2N aqueous hydrochloric acid
  5. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-672480c462aa4033b0631c18fdc733e7
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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