Triethylamine → 2-(Chloromethyl)-1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole

HRID 714633Notes

Reaction equation

HRID 714633 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=[C:6]1[CH2:13]O.C(N(CC)CC)C.S(Cl)([Cl:29])=O>ClCCl>[Cl:29][CH2:13][C:6]1[N:5]([CH2:4][C:3]2[C:2]([Cl:1])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl Chloride2×HCID 67410386[1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol

Product 1

HCID 674099292-(Chloromethyl)-1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

210 mg (0.70 mmol) of the compound from Example 37A were dissolved in 10 ml of dichloromethane, and 145 μl (1.04 mmol) of triethylamine and 61 μl (0.83 mmol) of thionyl chloride were added at 0° C. The mixture was stirred at RT for 24 h. A further 200 μl (2.72 mmol) of thionyl chloride were then added, and the mixture was stirred under reflux for 15 min. Under reduced pressure, the reaction mixture was then freed from all volatile components. This gave, in a purity of 88%, 200 mg (80% of theory) of the target compound, which was reacted further without any further purification.

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 15 min
  3. customThis gave, in a purity of 88%, 200 mg (80% of theory) of the target compound, which was reacted further without any further purification

Sources & evidence

ORD record
ord-7ca9cbf52d864006b20986c798521ac7
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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