4-(Trifluoromethoxy)benzoyl Chloride → N-[2-(5-Chloro-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

HRID 70921Notes

Reaction equation

HRID 70921 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[NH2:15][C:16]([CH3:30])([CH2:19][N:20]1[N:24]=[C:23]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:22]2=[N:21]1)[C:17]#[N:18]>C(Cl)Cl>[Cl:29][C:27]1[CH:26]=[CH:25][C:23]2=[N:24][N:20]([CH2:19][C:16]([NH:15][C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=3)([C:17]#[N:18])[CH3:30])[N:21]=[C:22]2[CH:28]=1

Participants

4

Reactant 2

HCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 666200452-amino-3-(5-chloro-2H-benzotriazol-2-yl)-2-methylpropionitrile

Product 1

HCID 25121566N-[2-(5-Chloro-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamideYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-trifluoromethoxybenzoyl chloride (0.34 g) was added to a solution of 2-amino-3-(5-chloro-2H-benzotriazol-2-yl)-2-methylpropionitrile (0.3 g) in dry DCM mixed with TEA (0.27 mL). The reaction mixture was stirred 48 hours at room temperature. Silica gel was added to the reaction mixture and solvent evaporated under reduced pressure. The resulting crude product loaded on silica gel was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid (0.3 g, 54%). Rf=0.7 (1:1 EA/heptane). MS (ES): M/Z [M+H]=424. 1H NMR: (400 MHz, DMSO-d6): 1.74 (s, 3H), 5.39-5.49 (m, 2H), 7.48 (dd, J=9.1, 1.9 Hz, 1H), 7.51 (br d, J=8.0 Hz, 2H), 7.93 (m, 2H), 8.01 (dd, J=9.1, 0.6 Hz, 1H), 8.13 (dd, J=1.9, 0.6 Hz, 1H) and 8.92 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −57.09 (s, 3F).

Workup

  1. additionSilica gel was added to the reaction mixture and solvent
  2. customevaporated under reduced pressure
  3. customwas purified by chromatography (SiO2, heptane/EA)

Sources & evidence

ORD record
ord-4404fd81c5b24bc08f4dda752e0d18de
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

Loading…