Ethyl isocyanate → HCID 10135168, compound

HRID 2113234Notes

Reaction equation

HRID 2113234 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-ff6088fe21ae48b59c09cbe9a33e3a95
Source dataset
uspto-grants-2009_04
Patent number
US07524969B2

Reaction notes

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