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

HRID 2113229Notes

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

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

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

Sources & evidence

ORD record: ord-e7646e70d0a4455b8579062964bd1fe2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524969B2

Reaction notes

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