Hydrochloric Acid → HCID 86746104, compound

HRID 1885230Notes

Reaction equation

HRID 1885230 reaction equation
CS[C:3]1[S:4]/[C:5](=[CH:9]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)/[C:6](=[O:8])[N:7]=1.Cl.[O:28]1CCCC1>>[F:24][C:23]([F:26])([F:25])[C:19]1[CH:18]=[C:17]([NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2/[CH:9]=[C:5]2/[C:6](=[O:8])[NH:7][C:3](=[O:28])[S:4]/2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86746105HCID 86746105, compound

Product 1

HCID 86746104HCID 86746104, compoundYield 83%

Procedure

To a room temperature solution of (Z)-2-methylthio-5-[[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]methylene]-4(5 H)-thiazolone (507 mg, 1.28 mmols) in 14 mL of tetrahydrofuran is added 14 mL of 10% aqueous hydrochloric acid. The mixture is heated at reflux for 30 minutes, then allowed to cool to room temperature. The mixture is partitioned between water and ethyl acetate. The organic phase is washed with saturated aqueous sodium bicarbonate followed by brine, then dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 390 mg (83%) of (Z)-5-[[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]methylene]-2,4-thiazolidinedione. An analytical sample is obtained by recrystallization from ethyl acetate and hexane; mp 213°-214° C. dec.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 minutes
  3. customThe mixture is partitioned between water and ethyl acetate
  4. washThe organic phase is washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77d628f760f84e41b0f857eea50d3db3
Source dataset
uspto-grants-1992_09
Patent number
US05143929

Reaction notes

Loading…