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

HRID 415708Notes

Reaction equation

HRID 415708 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-5782ecda6e114685aa86644c989f02db
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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