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

HRID 847082Notes

Reaction equation

HRID 847082 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) δ8.07 (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-416c2adb8ed744598ac333a154a06f16
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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