Thionyl Chloride → 2-Butyl-1-[4-(2-carbomethoxybenzoyl)benzyl]-4-chloro-5-(chloromethyl)-imidazole, hydrochloride salt

HRID 466435Notes

Reaction equation

HRID 466435 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([O:29][CH3:30])=[O:28])=[CH:16][CH:15]=2)[C:7]([CH2:11]O)=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:34])=O>C(Cl)(Cl)Cl>[ClH:10].[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([O:29][CH3:30])=[O:28])=[CH:18][CH:19]=2)[C:7]([CH2:11][Cl:34])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 198152912-Butyl-1-[4-(2-carbomethoxybenzoyl)benzyl]-4-chloro-5-hydroxymethylimidazole

Product 1

HCID 198154362-Butyl-1-[4-(2-carbomethoxybenzoyl)benzyl]-4-chloro-5-(chloromethyl)-imidazole, hydrochloride saltYield 103.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Butyl-1-[4-(2-carbomethoxybenzoyl)benzyl]-4-chloro-5-hydroxymethylimidazole (5.00 g, 11.3 mmol, 1 eq) was dissolved in 50 mL chloroform and to this solution was dropwise added thionyl chloride (4.13 mL, 56.6 mmol, 5 eq) with stirring at room temperature. After 4 hours, the solvent and excess thionyl chloride were removed by rotary evaporation. Toluene (100 mL) was added to the residue and the solvent again removed by rotary evaporation. Toluene was again added and while evaporating the second time, product crystallized from solution yielding 2.91 g of a white solid; m.p. 139.0°-143.5°. NMR (200 MHz, CDCl3) δ 8.07 (d, 1H, J=7 Hz); 7.80 (d, 2H, J=10 Hz); 7.68 (t, 1H, J=7 Hz); 7.58 (t, 1H, J=7 Hz); 7.35 (d, 1H, J=7 Hz); 7.13 (d, 2H, J=10 Hz); 5.43 (s, 2H); 4.42 (s, 2H); 3.67 (s, 3H); 2.96 (m, 2H); 1.75 (m, 2H); 1.39 (m, 2H); 0.88 (t, 2H, J=7 Hz). Mass Calcd. for C24H24Cl2N2O3 : 458.1162. Found: 458.1160.

Workup

  1. customthe solvent and excess thionyl chloride were removed by rotary evaporation
  2. additionToluene (100 mL) was added to the residue
  3. customthe solvent again removed by rotary evaporation
  4. additionToluene was again added
  5. customwhile evaporating the second time, product
  6. customcrystallized from solution

Sources & evidence

ORD record
ord-0f70668bdc4e43a0aa1503d8c719dd64
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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