3-(Trifluoromethyl)aniline → HCID 4465955, compound

HRID 1243667Notes

Reaction equation

HRID 1243667 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=2)=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 1441174-Fluoro-3-nitrophenyl isocyanate

Product 1

HCID 4465955HCID 4465955, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Fluoro-3-nitrophenyl isocyanate (15 g, 82.40 mmol) was dissolved in 200 mL of methylene chloride under a nitrogen atmosphere. A solution of 3-trifluoromethyl aniline (13.27 g, 82.40 mmol) dissolved in 50 mL of methylene chloride was added drop-wise. The reaction was left to stir for 12 hours. During this time, a yellow precipitate formed. This solid was collected by filtration and dried under vacuum to give 27.9 g of pure product (98% yield). 1H NMR (400 MHz CDCl3) δ: 7.25 (dd, 1H), 7.39–7.46 (m, 2H), 7.55 (d, 1H), 7.63–7.67 (m, 1H), 7.94 (s, 1H), 8.36 (dd, 1H), 9.14 (s, 1H), 9.21 (s, 1H). MS: m/z 366 (M+Na+).

Workup

  1. additionwas added drop-wise
  2. waitThe reaction was left
  3. customDuring this time, a yellow precipitate formed
  4. filtrationThis solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f74960cfe5e44b908477c881232a1230
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

Loading…