Triethylamine → 5-(Chloromethyl)-1-(2,6-dichlorobenzyl)-1H-imidazole

HRID 714632Notes

Reaction equation

HRID 714632 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][N:5]1[C:9]([CH2:10]O)=[CH:8][N:7]=[CH:6]1.C(N(CC)CC)C.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[Cl:26][CH2:10][C:9]1[N:5]([CH2:4][C:3]2[C:2]([Cl:1])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:16])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 67409440[1-(2,6-Dichlorobenzyl)-1H-imidazol-5-yl]methanol

Product 1

HCID 674100415-(Chloromethyl)-1-(2,6-dichlorobenzyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

45 mg (0.18 mmol) of the compound from Example 36A together with 27 mg (0.26 mmol) of triethylamine were dissolved in 1 ml of toluene, and 25 mg (0.21 mmol) of thionyl chloride were added dropwise at RT. The mixture was stirred at RT for 1 h. Under reduced pressure, the reaction mixture was freed from all volatile components. This gave 48 mg (99% of theory) of the target compound, which was reacted further without any further purification.

Workup

  1. customThis gave 48 mg (99% of theory) of the target compound, which was reacted further without any further purification

Sources & evidence

ORD record
ord-bac4823159dd4a1ab1e4ec62f7434e59
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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