Chloroform → HCID 13320313, compound

HRID 1462110Notes

Reaction equation

HRID 1462110 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)C.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=CC=1.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][SH:28])=[CH:25][CH:24]=1.B(F)(F)F.[CH3:35][CH2:36]OCC.[CH:40]([Cl:43])(Cl)Cl>C(O)(=O)C>[ClH:14].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][S:28][CH:4]([S:21][CH2:18][C:19]2[CH:20]=[CH:15][C:40]([Cl:43])=[CH:36][CH:35]=2)[CH2:5][N:6]2[CH:10]=[CH:9][N:8]=[CH:7]2)=[CH:25][CH:24]=1

Participants

7

Reactant 5

HCID 6212Chloroform2×HCID 7815p-ChlorothiophenolHCID 8000Boron trifluoride etherateHCID 804094-Chlorobenzyl mercaptanHCID 802714918999-43-4

Product 1

HCID 13320313HCID 13320313, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(2,2-diethoxyethyl)-1H-imidazole (3.68 g, 0.020 mole), 4-chlorothiophenol (2.88 g, 0.020 mole) and 4-chlorobenzyl mercaptan (3.16 g, 0.020 mole) in chloroform (50 ml) was added dropwise during 30 minutes to a stirred, refluxing mixture of boron trifluoride etherate (4.8 ml, 0.036 mole) and acetic acid (10 ml) in chloroform (30 ml). The mixture was stirred under reflux for 18 hours and concentrated. The residue was partitioned between diethyl ether and cold aqueous sodium hydroxide. The organic layer was washed with water (2×) followed by brine and dried over Na2SO4. Hydrogen chloride was bubbled into the ethereal filtrate to afford a mixture of the hydrochloride salts of the three possible mercaptals. The mixture was crystallized from ethanol-ether to yield 1.4 g of 1-[2,2-bis(4-chlorobenzylthio)ethyl]-1H-imidazole hydrochloride, mp 180°-183°. Dilution of the mother liquor with additional ether provided 2.2 g of the title compound, mp 135°-137°, which melted at 136°-139° after recrystallization from chloroform-ether.

Workup

  1. temperaturerefluxing
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between diethyl ether and cold aqueous sodium hydroxide
  5. washThe organic layer was washed with water (2×)
  6. dry with materialdried over Na2SO4
  7. customHydrogen chloride was bubbled into the ethereal filtrate
  8. customto afford
  9. customThe mixture was crystallized from ethanol-ether

Sources & evidence

ORD record
ord-0a9c80801e7f41619edf2d8126dc2841
Source dataset
uspto-grants-1984_07
Patent number
US04458079

Reaction notes

Loading…