Water → HCID 86743861, compound

HRID 2073517Notes

Reaction equation

HRID 2073517 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.[C:19]1(C)[C:20]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=1.O.N1C=CC=C[CH:32]=1>>[S:25]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1)([C:20]1[CH:19]=[CH:24][C:23]([CH3:32])=[CH:22][CH:21]=1)(=[O:26])=[O:27]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 20703757HCID 20703757, compound

Product 1

HCID 86743861HCID 86743861, compound

Procedure

A solution of 5-[4-(2-Hydroxyethoxy)Benzyl]-2,4-Thiazolidinedione (5.34 g) in pyridine (50 ml) was cooled to below 5° C. Toluenesulphonyl chloride (3.82 g) was added portionwise to the stirred solution and the mixture was allowed to stand overnight at below 5° C. The solution was poured into water (200 ml) and extracted with dichloromethane (2×200 ml). The organic extracts washed with 5% hydrochloric acid solution and water, dried (MgSO4), filtered and evaporated under reduced pressure to give an oil which was used without further purification.

Workup

  1. extractionextracted with dichloromethane (2×200 ml)
  2. washThe organic extracts washed with 5% hydrochloric acid solution and water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an oil which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-5bd1c93201b742d8aaa1d24bdbf0a28d
Source dataset
uspto-grants-1990_04
Patent number
US04918091

Reaction notes

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