Water → HCID 53959327, compound

HRID 2379897Notes

Reaction equation

HRID 2379897 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]O)[CH:25]=3)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.C1(C)C(S([Cl:50])(=O)=O)=CC=CC=1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][Cl:50])[CH:25]=3)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8623o-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 18956343HCID 18956343, compound

Product 1

HCID 53959327HCID 53959327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part C. A solution of the alcohol prepared above (5.96 g, 13.8 mmol), diisopropylethylamine (2.90 mL, 16.6 mmol) and toluenesulfonyl chloride (2.89 g, 15.2 mmol) in tetrahydrofuran (30 mL) was heated to reflux for 18 hours. The mixture was cooled, and poured into water (150 mL). This was extracted with methylene chloride (2×150 mL), and the extracts were combined, dried over magnesium sulfate and evaporated. The residual oil was separated by flash chromatography (3:7 ethyl acetate-hexane)to afford the product, 4,5-bis (4-methoxyphenyl)-2-[3-(chloro-methyl)benzyl]thio-1H-imidazole, as a foam upon vacuum pumping (2.24 g, 4.96 mmol, 36%). 1H NMR (CDCl3): 8.94 (1H, br s); 7.70-7.09 (8H, m); 6.84 (4H, d, J=8.8 Hz); 4.51 (2H, s); 4.19 (2H, s); 3.81 (6H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. extractionThis was extracted with methylene chloride (2×150 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residual oil was separated by flash chromatography (3:7 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-be13353073ec4f42bb9fd83c90551204
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

Loading…