Methyl iodide → 3-(4-chlorophenyl)-N-((piperidin-1-yl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl ester

HRID 1822120Notes

Reaction equation

HRID 1822120 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19](=[S:30])[NH:20][S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[CH2:31](N(CC)CC)C.CI>CC(C)=O>[CH3:31][S:30][C:19]([N:10]1[CH2:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9]1)=[N:20][S:21]([N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)(=[O:22])=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 22267339HCID 22267339, compound

Product 1

HCID 690559963-(4-chlorophenyl)-N-((piperidin-1-yl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl esterYield 90.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Part B: To a stirred solution of 3-(4-chlorophenyl)-4-phenyl-N-((piperidin-1-yl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-thiocarboxamide (30 gram, 64.9 mmol) in acetone (1 L) is added triethylamine (18.0 mL, 130 mmol). To the resulting yellow solution is added methyl iodide (9.12 g, 64 mmol) and the resulting solution is stirred for 16 hours at room temperature. The formed precipitate is removed by filtration. The filtrate is washed with water, concentrated in vacuo to give a yellow solid. Recrystallisation from MTBE gives 3-(4-chlorophenyl)-N-((piperidin-1-yl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidothioic acid methyl ester (27.9 gram, 90% yield). MP: 192-194° C.

Workup

  1. customThe formed precipitate is removed by filtration
  2. washThe filtrate is washed with water
  3. concentrationconcentrated in vacuo
  4. customto give a yellow solid
  5. customRecrystallisation from MTBE

Sources & evidence

ORD record
ord-4b44562cba9d48a4ba38664ca2afdc45
Source dataset
uspto-grants-2009_10
Patent number
US07608718B2

Reaction notes

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