Potassium Carbonate → 2-(3-Chloro-2-methylph-enyl-thiomethyl)-2-imidazoline hydrochloride

HRID 653657

Reaction equation

HRID 653657 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:12][C:13]1[NH:14][CH2:15][CH2:16][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:1].[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([S:8][CH2:12][C:13]2[NH:17][CH2:16][CH2:15][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27609282-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochlorideHCID 148782363-Chloro-2-methylbenzenethiol

Product 1

HCID 148782382-(3-Chloro-2-methylph-enyl-thiomethyl)-2-imidazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.55 g (35 mmol) of 3-chloro-2-methyl-thiophenol, 5.43 g (35 mmol) of 2-chloromethyl-2-imidazoline hydrochloride and 5 g of potassium carbonate are stirred in 40 ml of ethanol at room temperature. After 25 h, the mixture is filtered and the filtrate is concentrated to dryness. The crude product is purified by column chromatography on silica gel. After the eluting agent has been stripped off, ethanolic hydrochloric acid is added to the residue and the product is precipitated by addition of ether. White crystals of melting point 208°-209° C. are obtained.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe crude product is purified by column chromatography on silica gel
  4. additionethanolic hydrochloric acid is added to the residue
  5. customthe product is precipitated by addition of ether
  6. customWhite crystals of melting point 208°-209° C. are obtained

Sources & evidence

ORD record
ord-8929725e1b2f4869a090178749328139
Source dataset
uspto-grants-1992_07
Patent number
US05128361

Linked notes

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