Methylamine → 5-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-1-methyl-4-isopropyl-1H-imidazole

HRID 1416021Notes

Reaction equation

HRID 1416021 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH3:20])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[CH3:21]N.[C:23](#[N:25])C>>[Cl:19][C:14]1[CH:13]=[C:12]([S:11][C:5]2[N:4]([CH3:20])[C:3]([CH2:2][N:25]([CH3:23])[CH3:21])=[N:7][C:6]=2[CH:8]([CH3:10])[CH3:9])[CH:17]=[C:16]([Cl:18])[CH:15]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 6342AcetonitrileHCID 221306052-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole

Product 1

HCID 4739875-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-1-methyl-4-isopropyl-1H-imidazoleYield 95%

Procedure

A mixture of 0.15 g (0.43 mmol)of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (28a), 1 ml of acetonitrile and 1.5 ml of a 50% methylamine aqueous solution was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with diethyl ether. The extract was washed with water and with saturated brine and dried over potassium carbonate. The solvent was distilled off under reduced pressure, and the residue was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:4)to obtain 0.148 g of (Compound I-78)(yield 95%). Oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with diethyl ether
  3. washThe extract was washed with water and with saturated brine
  4. dry with materialdried over potassium carbonate
  5. distillationThe solvent was distilled off under reduced pressure
  6. custommethylene chloride=1:4)to obtain 0.148 g of (Compound I-78)(yield 95%)

Sources & evidence

ORD record
ord-0f0a65c1a7c5418ba7a681e2518d2a56
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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