4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde → HCID 89723786, compound

HRID 1404875Notes

Reaction equation

HRID 1404875 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH:25]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37]([NH:39][NH2:40])=[S:38])[CH2:29][CH2:28][CH2:27][CH2:26]1>CO>[CH:25]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37]([NH:39]/[N:40]=[CH:19]/[C:18]2[CH:21]=[CH:22][C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=4)[N:11]=3)=[CH:16][CH:17]=2)=[S:38])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehydeHCID 86691481HCID 86691481, compound

Product 1

HCID 89723786HCID 89723786, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (0.58 g, 1.7 mmol) and N-(2-cyclopentylphenyl)hydrazinecarbothioamide (0.41 g, 1.7 mmol) in a 100 mL roundbottom flask equipped with a magnetic stir bar and reflux condenser was added methanol (17 mL), and the reaction was heated to 50° C. and stirred overnight. The reaction was cooled to room temperature and the resulting solid was filtered, washed with methanol and dried under vacuum (25 in Hg) at 55° C. to give the title compound (795 mg, 1.44 mmol, 83% yield) as a yellow solid: mp 213-216° C.; 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 9.11 (s, 1H), 8.60 (s, 1H), 8.26 (d, J=8.4 Hz, 2H), 7.91 (s, 1H), 7.86-7.71 (m, 5H), 7.40 (dd, J=8.8, 6.4 Hz, 3H), 7.35-7.27 (m, 2H), 3.22 (t, J=8.0 Hz, 1H), 2.13 (d, J=2.5 Hz, 2H), 1.90-1.59 (m, 6H); ESIMS m/z 551 ([M+H]+).

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationthe resulting solid was filtered
  5. washwashed with methanol
  6. customdried under vacuum (25 in Hg) at 55° C.

Sources & evidence

ORD record
ord-998b9d73958a40c1904165cc962e0c72
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

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