Imidazole → HCID 23317797, compound

HRID 1981828Notes

Reaction equation

HRID 1981828 reaction equation
[CH:1]1([O:6][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])([CH2:10]OS(C)(=O)=O)[C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.CN(C=O)C>O>[CH:1]1([O:6][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])([CH2:10][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)[C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 13455550HCID 13455550, compound

Product 1

HCID 23317797HCID 23317797, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60.7 g (0.188 mol) 2-cyclopentyloxy-2-(2-methylphenyl)-3-methylsulfonyloxy-propanenitrile, 63.9 g (0.938 mol) imidazole and 3.88 ml DMF are stirred for six hours at 160° C. bath temperature. They are then poured into 200 ml water, extracted twice--each time with 200 ml methylene chloride--and the organic phase is then dried with MgSO4. It is then rotated in a vacuum after which the oil is dissolved in 100 ml isopropanol and then reacted dropwise with 10 ml 100% nitric acid, with cooling with ice. Next follows 20 minutes after-stirring with RT, addition of 200 ml acetic ester, and evacuation in a vacuum. In this manner 30.7 g of the title compound are obtained, MP: 160° C. (decomposition).

Workup

  1. extractionextracted twice
  2. dry with materialeach time with 200 ml methylene chloride--and the organic phase is then dried with MgSO4
  3. dissolutionis dissolved in 100 ml isopropanol
  4. customreacted dropwise with 10 ml 100% nitric acid
  5. temperaturewith cooling with ice

Sources & evidence

ORD record
ord-16aeef71b8c043c6bebcab4081261a07
Source dataset
uspto-grants-1986_06
Patent number
US04594095

Reaction notes

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