Methyl iodide → HCID 178503863, compound

HRID 586561Notes

Reaction equation

HRID 586561 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([NH:8][C:9]([NH:11][C:12]2[C:13]([CH3:19])=[N:14][N:15]([CH3:18])[C:16]=2[CH3:17])=[S:10])[CH:7]=1.[CH3:21]I>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([NH:8]/[C:9](=[N:11]\[C:12]2[C:13]([CH3:19])=[N:14][N:15]([CH3:18])[C:16]=2[CH3:17])/[S:10][CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 98578071-(5-Chloro-2-methyl-phenyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea

Product 1

HCID 178503863HCID 178503863, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under anhydrous conditions, a solution of 1-(5-Chloro-2-methyl-phenyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea (2.3 g, 7.5 mmol) produced in example 8 and methyl iodide (0.94 mL, 15 mmol) in 70 mL of acetone was stirred at ambient temperature for 64 hours. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution. The organic phase was washed with dilute Na2S2O3 and dried (Na2SO4). Removal of solvent and crystallization of the residue from Et2O provided 1.78 g of title compound as a white solid (74% of theory, m.p. 134-135° C.).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  3. washThe organic phase was washed with dilute Na2S2O3
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent and crystallization of the residue from Et2O

Sources & evidence

ORD record
ord-a5e3c8b2da554bf685abb80ca8c18a99
Source dataset
uspto-grants-2005_08
Patent number
US06936630B2

Reaction notes

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