3-(Trifluoromethyl)phenyl isocyanate → HCID 17267351, compound

HRID 1091484Notes

Reaction equation

HRID 1091484 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[C:11]=[O:12]>C1COCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]([NH:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)=[O:12])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 17267351HCID 17267351, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-fluoroaniline (3.0 g, 15.8 mmol) in THF (15 mL) was added 1-isocyanato-3-(trifluoromethyl)benzene (3.55 g, 18.9 mmol). The reaction was stirred at room temperature overnight. Solid product was present in the reaction vessel. Product was further precipitated by the addition of 1:2 ether/hexanes. The solids were collected by filtration, dried under hi vacuum and found to be clean title compound in 60% yield. 1H-NMR (DMSO-d6) δ 9.44 (s, 1H), 8.76 (d, J=1.2 Hz, 1H), 8.12 (t, J=8.7, 1H), 8.05 (s, 1H), 7.64-7.37 (m, 5H); MS [M+H]+=378.9, LCMS RT=3.92 min.

Workup

  1. customProduct was further precipitated by the addition of 1:2 ether/hexanes
  2. filtrationThe solids were collected by filtration
  3. customdried under hi vacuum

Sources & evidence

ORD record
ord-229d197e205a488aba5dec22d39f83d2
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

Loading…