Thionyl Chloride → 2-Chloro-5-chloromethyl-6-trifluoromethyl-1-(2,4,6-trimethyl-phenyl)-1H-imidazo[1,2-a]imidazole

HRID 1349431Notes

Reaction equation

HRID 1349431 reaction equation
[Cl:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[N:5]([CH:15]=1)[C:6]([CH2:13]O)=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=2.S(Cl)([Cl:27])=O>ClCCl>[Cl:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[N:5]([C:6]([CH2:13][Cl:27])=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21916271[6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazol-3-yl]-methanol

Product 1

HCID 219160952-Chloro-5-chloromethyl-6-trifluoromethyl-1-(2,4,6-trimethyl-phenyl)-1H-imidazo[1,2-a]imidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazol-3-yl]-methanol (614.8 mg, 1.718 mmol) and thionyl chloride (1.25 mL) in dichloromethane was stirred at 0° C. for 15 min. Thionyl chloride and the solvent were removed in vacuo and the residue was dried under high vacuum to yield the desired product as a yellow solid (646.3 mg, 100%). LC/MS: tR=1.46 min., MS: [MH−Cl+OMe]=373.

Workup

  1. customThionyl chloride and the solvent were removed in vacuo
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4de1fa377b1e4a37a992acaee9502794
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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