Ethyl isocyanate → HCID 10135168, compound

HRID 1643513Notes

Reaction equation

HRID 1643513 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

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 86591941HCID 86591941, compound

Product 1

HCID 10135168HCID 10135168, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

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).

Workup

  1. temperaturewas refluxed for 4 h
  2. customSolvent was removed under reduced pressure
  3. customto obtain an oil, which
  4. washThe resulting solution was washed with H2O, saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. customto yield a crude product which
  8. customwas purified by preparative TLC (EtOAC:hexanes, 1:3)

Sources & evidence

ORD record
ord-e5453d10c6e146bea8061995e5e920b9
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

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