Hydrochloric Acid → HCID 44176497, compound

HRID 1673047Notes

Reaction equation

HRID 1673047 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([C:22]([NH:24][NH2:25])=O)[N:19]=[C:18]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH3:36][N:37]=[C:38]=[S:39].Cl>C([O-])([O-])=O.[K+].[K+]>[CH3:36][N:37]1[C:38](=[S:39])[NH:25][N:24]=[C:22]1[C:20]1[N:19]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=3)=[CH:12][CH:13]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 59240015HCID 59240015, compound

Product 1

HCID 44176497HCID 44176497, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

To a suspension of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (215 mg, 0.430 mmol) in 8 mL 10% K2CO3 solution was added methyl isothiocyanate (0.06 mL, 0.877 mmol) via syringe. The reaction was refluxed 12 h and cooled to room temperature. The reaction was neutralized at 0° C. with 1M HCl and then extracted 3×10 mL with ethyl acetate. The combined organic layers were dried with MgSO4 and the solvent removed in vacuo. The crude residue was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 4-methyl-3-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1H-1,2,4-triazole-5(4H)-thione (27 mgs, II %) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 13.89 (s, 1H), 8.37 (s, 1H), 8.15-8.14 (m, 1H), 8.05-8.02 (m, 1H), 7.93-7.89 (m, 2H), 7.85 (d, J=8.58 Hz, 2H), 7.75-7.73 (m, 1H), 7.72-7.68 (m, 2H), 7.62-7.59, (m, 1H), 7.41 (d, J=8.58 Hz, 2H), 3.78 (s, 3H), 3.28 (s, 3H); MS (ES): 556.0 [M+H]+ and 578.3 [M+Na]+.

Workup

  1. temperatureThe reaction was refluxed 12 h
  2. extractionextracted 3×10 mL with ethyl acetate
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. customthe solvent removed in vacuo
  5. customThe crude residue was absorbed onto silica
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-71c1a063537c4018be1bda14f0bc240c
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

Loading…