Trifluoroacetic acid → 5-Ethyl-4-methylthiazol-2-amine

HRID 1009035Notes

Reaction equation

HRID 1009035 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH2:14][CH3:15])=[C:11]([CH3:13])[N:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:14]([C:10]1[S:9][C:8]([NH2:7])=[N:12][C:11]=1[CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86630952HCID 86630952, compound

Product 1

HCID 127359565-Ethyl-4-methylthiazol-2-amineYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above prepared (5-ethyl-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.394 g, 1.626 mmol) was dissolved in 8 mL of CH2Cl2 and treated with 1.5 mL of TFA. After 2 h at RT all starting material had disappeared. The reaction mixture was then poured onto icewater/NaHCO3, twofold extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/ethyl acetate=1/1) yielded 0.200 g of the title compound as light brown viscous oil.

Workup

  1. extractiontwofold extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4545e476a85644869e865b9e155765b3
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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