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

HRID 1643508Notes

Reaction equation

HRID 1643508 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.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>[NH2:1][C:2]1[S:3][C:4]([C:12]([OH:13])([C:14]([F:17])([F:16])[F:15])[C:11]([F:19])([F:18])[F:10])=[CH:5][N:6]=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 73.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A catalytic amount of molecular sieves powder (4A) was added to a mixture of 2-aminothiazole 200 mg (2 mmol) and hexafluoroacetone trihydrate (880 mg, 4 mmol). The mixture was heated at 100° C. for 8 h. Ethyl acetate was added and the mixture was filtered. Organic solvents were evaporated under reduced pressure. The residue was recrystallized in THF and hexanes to afford the title product (389 mg) as a white solid. 1H NMR (DMSO-d6) δ7.12 (s, 1H), 7.45 (brs, 2H), 8.85 (s, 1H); ESIMS: m/z 267 (M+H).

Workup

  1. filtrationthe mixture was filtered
  2. customOrganic solvents were evaporated under reduced pressure
  3. customThe residue was recrystallized in THF

Sources & evidence

ORD record
ord-0406041cc69c4b09b9543ebd85d17634
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

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