2-Aminothiazole → 2-(2-AMINO-1,3-THIAZOL-5-YL)-1,1,1,3,3,3-HEXAFLUOROPROPAN-2-OL

HRID 1807806Notes

Reaction equation

HRID 1807806 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].O.O.O.[F:10][C:11]([F:19])([F:18])[C:12]([C:14]([F:17])([F:16])[F:15])=[O:13]>C(OCC)(=O)C>[NH2:6][C:2]1[S:1][C:5]([C:12]([OH:13])([C:14]([F:17])([F:16])[F:15])[C:11]([F:19])([F:18])[F:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 36719Hexafluoroacetone trihydrate

Product 1

HCID 23180662-(2-AMINO-1,3-THIAZOL-5-YL)-1,1,1,3,3,3-HEXAFLUOROPROPAN-2-OLYield 32.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Thiazol-2-amine (150 mmol, 15 g), 4 Å powdered molecular sieves (1 g) and hexafluoroacetone trihydrate (300 mmol, 65.9 g) were combined and heated to 100° C. for 16 hours. The reaction mixture was cooled, diluted with ethyl acetate (200 mL) and filtered through celite. The filtrate was concentrated under reduced pressure to give a brown liquid which crystallised on standing. The solid was collected by filtration, washed with heptane (100 mL) then diethyl ether (50 mL) and dried under vacuum to afford the title compound (12.9 g). MS (ESI) m/z 266.7 [M+H]+

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a brown liquid which
  5. customcrystallised
  6. filtrationThe solid was collected by filtration
  7. washwashed with heptane (100 mL)
  8. dry with materialdiethyl ether (50 mL) and dried under vacuum

Sources & evidence

ORD record
ord-9b2a59b4a77f43ec80ebbf9ed24793b7
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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