HCID 19811372, compound → HCID 19811324, compound

HRID 373077Notes

Reaction equation

HRID 373077 reaction equation
[C:1]([C:9]1[CH:32]=[CH:31][C:12]2[N:13](CC3C=CC(OC)=CC=3)[C:14](=[O:21])[N:15]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.O>[C:1]([C:9]1[CH:32]=[CH:31][C:12]2[NH:13][C:14](=[O:21])[N:15]([CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19811372HCID 19811372, compound

Product 1

HCID 19811324HCID 19811324, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.11 g of 5-benzoyl-1,3-dihydro-3-(2-dimethylaminoethyl)-1-(4-methoxybenzyl)-2H-benzimidazol-2-one in 20 ml of acetonitrile and 7 ml of water was added 6.43 g of ceric ammonium nitrate. The reaction mixture was stirred at 60° C. for 4 hours, diluted with water and washed with ethyl acetate. After alkalization to pH 9 with 10% sodium hydroxide, the basic material was extracted with chloroform and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo afforded the crude material which was chromatographed on silica gel. Elution with chloroformmethanol (10:1) gave 40 mg of 6-benzoyl-1,3-dihydro-1-(2-dimethylaminoethyl)-2H-benzimidazol-2-one.

Workup

  1. washwashed with ethyl acetate
  2. extractionAfter alkalization to pH 9 with 10% sodium hydroxide, the basic material was extracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of the solvent in vacuo
  5. customafforded the crude material which
  6. customwas chromatographed on silica gel
  7. washElution with chloroformmethanol (10:1)

Sources & evidence

ORD record
ord-0a3ea74490cc4189b3e6f2aab8296d44
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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