Hydrochloric Acid → HCID 15729166, compound

HRID 1656966Notes

Reaction equation

HRID 1656966 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[CH:8][N:9]=1)(=O)C.Cl>C(O)C>[NH2:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15729165HCID 15729165, compound

Product 1

HCID 15729166HCID 15729166, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetamido-5-(2,4-difluorophenylthio)thiazole (14.8 g) in a mixture of ethanol (150 ml) and concentrated hydrochloric acid (15 ml) was refluxed for 1.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The solution was adjusted to pH 12 using aqueous sodium hydroxide with stirring under ice-cooling. The mixture was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The organic layer was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel, 230-400 mesh, Nakarai) (300 g) and eluted with a mixture of chloroform and methanol (100:1). The fractions containing the objective compound were combined and evaporated to dryness in vacuo to give 2-amino-5-(2,4-difluorophenylthio)thiazole (6.26 g, yield: 49.6%). mp: 116°-117° C. IR (Nujol): 3410, 3090, 1625, 1600, 1515 cm-1NMR (DMSO-d6, 60 MHZ, ppm): 7.07-7.76 (6H, m) MASS: M+2 246, M 244, m/e 157

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. extractionThe mixture was extracted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customto give solid
  11. washeluted with a mixture of chloroform and methanol (100:1)
  12. additionThe fractions containing the objective compound
  13. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d525bcfd80fc4aa79d7fac5ec935aeef
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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