Ethyl isocyanate → HCID 10135168, compound

Reaction equation

[CH2:1]([NH:5][C:6]1[S:7][C:8]([C:11]([OH:20])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])=[CH:9][N:10]=1)[CH2:2][CH2:3][CH3:4].[CH2:21]([N:23]=[C:24]=[O:25])[CH3:22]>C1C=CC=CC=1.CCOC(C)=O>[CH2:1]([N:5]([C:6]1[S:7][C:8]([C:11]([OH:20])([C:12]([F:13])([F:14])[F:15])[C:16]([F:19])([F:17])[F:18])=[CH:9][N:10]=1)[C:24]([NH:23][CH2:21][CH3:22])=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

Procedure

To a mixture of 2-[2-(butylamino)-1,3-thiazol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol (65 mg, 0.202 mmol) obtained from step 1 in benzene (2 ml) was added ethyl isocyanate (24 μL, 0.3 mmol) under a nitrogen atmosphere The reaction mixture was refluxed for 4 h. Solvent was removed under reduced pressure to obtain an oil, which was dissolved in EtOAc. The resulting solution was washed with H2O, saturated NaHCO3 and brine, and dried over MgSO4. The solvent was evaporated to yield a crude product which was purified by preparative TLC (EtOAC:hexanes, 1:3) to afford the corresponding product as a white solid (31 mg). 1H NMR δ0.92 (t, 3H), 1.20 (t, 3H), 1.37 (m, 2H) 1.67 (m, 2H), 3.37 (q, 2H), 3.83 (t, 2H), 4.24 (brs, 1H), 7.50 (s, 1H), 8.60 (brs, 1H); ESIMS: m/z 392 (M−H).