Phenol → HCID 69455603, compound

HRID 916088Notes

Reaction equation

HRID 916088 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11][C:12]1[N:16]([CH2:17][CH2:18][OH:19])[C:15]2[CH:20]=[C:21]([CH3:25])[C:22]([CH3:24])=[CH:23][C:14]=2[N:13]=1.CCOC(/N=N/C(OCC)=O)=O.[C:39]1(O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN1CCOCC1>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11][C:12]1[N:16]([CH2:17][CH2:18][O:19][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:15]2[CH:20]=[C:21]([CH3:25])[C:22]([CH3:24])=[CH:23][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 5462977Diethyl azodicarboxylateHCID 69454732HCID 69454732, compound

Product 1

HCID 69455603HCID 69455603, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

To 2-((1-(2-hydroxyethyl)-5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester (45 mg, 0.23 mmol) in N-methylmorpholine (3 ml), Pph3 (62 mg, 0.24 mmol) and DEAD (10.6 ml, 40% in toluene, 0.24 mmol) were added and the mixture was stirred at room temperature. After 10 minutes, phenol (11.3 mg, 0.12 mmol) was added thereto, which was stirred at room temperature for 12 hours. The solvent was evaporated and the residue was purified by thin layer chromatography (hexane:ethyl acetate=1:1) to obtain 2-((5,6-dimethyl-1-(2-phenoxyethyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester (44 mg, yield 81%).

Workup

  1. stirringwhich was stirred at room temperature for 12 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by thin layer chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fbae69c765db4cd29943c6dab32f1306
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

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