Trifluoroacetic acid → 4-[2-(4-Fluorophenoxy)ethyl]-1,3-thiazol-2-amine

HRID 1430640Notes

Reaction equation

HRID 1430640 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:19]=1)(C)(C)C>C(Cl)Cl>[F:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][C:18]2[N:19]=[C:15]([NH2:14])[S:16][CH:17]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59363813HCID 59363813, compound

Product 1

HCID 20500224-[2-(4-Fluorophenoxy)ethyl]-1,3-thiazol-2-amineYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (12 ml) was added to a solution of {4-[2-(4-Fluoro-phenoxy)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (2.55 g, 7.5 mmol) in DCM (100 ml) at 0° C. and stirred at r.t. for 4 h. The reaction was quenched with saturated aqueous NaHCO3 solution (15 ml) and extracted in DCM, dried over Na2SO4, evaporated under reduced pressure to yield 4-[2-(4-Fluoro-phenoxy)-ethyl]-thiazol-2-ylamine (1.55 g, 86%). 1H NMR (400 MHz, CDCl3): δ 3.0 (t, J=6.8 Hz, 2H), 4.20 (t, J=6.8 Hz, 2H), 4.88 (brs, 2H), 6.26 (s, 1H), 6.83-6.86 (m, 2H), 6.94-6.98 (m, 2H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution (15 ml)
  2. extractionextracted in DCM
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c185f36c82554066960766b233b1bf96
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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