2-(Trifluoromethyl)phenyl isocyanate → HCID 57495607, compound

HRID 1092338Notes

Reaction equation

HRID 1092338 reaction equation
[CH:1]1([NH:4][CH:5]([CH:8]([CH3:10])[CH3:9])[CH2:6][OH:7])[CH2:3][CH2:2]1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>C1COCC1>[CH:1]1([N:4]([CH:5]([CH2:6][OH:7])[CH:8]([CH3:10])[CH3:9])[C:20]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([F:11])([F:22])[F:23])=[O:21])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 57495606HCID 57495606, compound

Product 1

HCID 57495607HCID 57495607, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of crude 2-cyclopropylamino-3-methyl-butan-1-ol (195 mg) in THF (10 mL) was slowly added a solution of 2-trifluoromethylphenylisocyanate (225 mg) in THF (3 mL) at 0° C. The mixture was then heated to 60° C. for 12 hours. After cooling, the solution was concentrated in vacuo and the residue was purified by flash chromatography using ethyl acetate/heptane 1:1 as an eluent to give the desired material as a colorless solid (245 mg). MS (ESI): 331.3 (MH+).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated in vacuo
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6aaf189f65654d899ffc7b08f867cd18
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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