Acetaldehyde → HCID 22258232, compound

HRID 1610833Notes

Reaction equation

HRID 1610833 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]1=O.[C:10]([O-])(=O)[CH3:11].[NH4+:14].C(=O)C.[Cl-].[Na+].[NH3:20]>CS(C)=O>[CH3:11][C:10]1[NH:20][C:4]2[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[C:3]=2[N:14]=1

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 222AmmoniaHCID 5234Sodium ChlorideHCID 517165Ammonium AcetateHCID 33213603-Methylcyclohexane-1,2-dione

Product 1

HCID 22258232HCID 22258232, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

20.0 g (0.159 mol) of 3-Methyl-1,2-cyclohexanedione and 183.31 g (2.38 mol) of ammoniumacetate are dissolved in 760 ml DMSO. A solution of 27.94 g (0.34 mol) acetaldehyde dissolved in 40 ml DMSO is dropped to the reaction mixture. The reaction is heated for 20 minutes to 40° C., 20 minutes to 60° C. and 40 minutes to 80° C. The reaction is allowed to cool down to rt. 2.5 l saturated sodium chloride solution and ammonia are added to reach a pH of 8-9. The solution is extracted with ethyl acetate and the organic phases are dried over sodium sulfate. The solvent is evaporated under vacuum. The crystalls are filtrated and washed with ethyl acetate and diethyl ether to yield 10.3 g (43.3% of th.) 2,4-Dimethyl-4,5,6,7-tetrahydro-1H-benzimidazole.

Workup

  1. additionis dropped to the reaction mixture
  2. temperatureThe reaction is heated for 20 minutes to 40° C., 20 minutes to 60° C. and 40 minutes to 80° C
  3. extractionThe solution is extracted with ethyl acetate
  4. dry with materialthe organic phases are dried over sodium sulfate
  5. customThe solvent is evaporated under vacuum
  6. filtrationThe crystalls are filtrated
  7. washwashed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-f9765ab7993941fe9dd4be146d30532a
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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