Water → HCID 86609610, compound

HRID 273365Notes

Reaction equation

HRID 273365 reaction equation
CS([O:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=2[N:10]=[C:9]1[C:21]([F:24])([F:23])[F:22])(=O)=O.[CH2:25]([O:27][CH:28]([CH2:34][C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1)[C:29]([O:31][CH2:32]C)=[O:30])[CH3:26].C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1>[F:22][C:21]([F:24])([F:23])[C:9]1[N:8]([CH2:7][CH2:6][O:5][C:38]2[CH:37]=[CH:36][C:35]([CH2:34][CH:28]([O:27][CH2:25][CH3:26])[C:29]([O:31][CH3:32])=[O:30])=[CH:40][CH:39]=2)[C:12]2[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 86609609HCID 86609609, compound

Product 1

HCID 86609610HCID 86609610, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[2,5-bis(trifluoromethyl)-1H-benzimidazol-1-yl]ethyl methanesulfonate (1.88 g, 5 mmol) and ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate (1.19 g, 5 mmol) were taken in toluene (20 ml) and K2CO3 (1.38 g, 10 mmol) was added. The reaction mixture was heated under reflux for 30 hrs. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The organic layer was dried and evaporated to the product which was purified by column chromatography on silica gel using ethyl acetate and hexanes as the solvent system (2.01 g, 77%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 hrs
  3. extractionthe product was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated to the product which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ec46f832d11f4cdaa7890dda708e1090
Source dataset
uspto-grants-2008_11
Patent number
US07456293B2

Reaction notes

Loading…