Hydrochloric Acid → HCID 86675817, compound

HRID 59882Notes

Reaction equation

HRID 59882 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[N:21]=2)=[CH:16][CH:15]=1)[C:3]([NH:5]C(=O)C1C=CC=CC=1)=[S:4].[OH-].[Na+].Cl>CO>[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:27][CH:26]=3)[N:21]=2)=[CH:16][CH:15]=1)[C:3]([NH2:5])=[S:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86675818HCID 86675818, compound

Product 1

HCID 86675817HCID 86675817, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a 100 mL round bottom flask containing MeOH (23 mL) was added N-(methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)carbamothioyl)benzamide (2.8 g, 5.63 mmol) and sodium hydroxide (5.6 mL of a 2 N solution, 11.3 mmol), and the solution was heated at 65° C. for 3.5 hours. Another 20 mL (40 mmol) of 2N NaOH was then added and heating was continued for 6 hours. Upon cooling the solution was neutralized by addition of 2N HCl, and the resulting yellow solid was collected by vacuum filtration to give 1-methyl-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea as a yellow solid (1.073 g, 47%): mp 142-152° C.; 1H NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 8.36-8.24 (m, 2H), 7.81 (d, J=9.0 Hz, 2H), 7.46-7.33 (m, 4H), 5.62 (s, 2H), 3.73 (s, 3H); ESIMS m/z 393 ([M+H]+).

Workup

  1. temperatureheating
  2. temperatureUpon cooling the solution
  3. filtrationthe resulting yellow solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-4f35db2af77c4ede9920b3a4e24934ae
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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