Sulfuric Acid → 1-Benzhydryl-2-Benzoylazetidine

HRID 1390959Notes

Reaction equation

HRID 1390959 reaction equation
S(=O)(=O)(O)O.[CH:6]([N:19]1[CH2:22][CH2:21][CH:20]1[C:23](=N)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-:32].[Na+]>CO>[CH:6]([N:19]1[CH2:22][CH2:21][CH:20]1[C:23](=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 203453011-Benzhydryl-2-benzimidoylazetidine

Product 1

HCID 203452751-Benzhydryl-2-Benzoylazetidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 68 ml of 3.6N aqueous sulfuric acid to a stirred solution of 40.0 g of 1-benzhydryl-2-benzimidoylazetidine in 800 ml. of methanol. Stir under a nitrogen atmosphere for 1.5 hours at room temperature. Slowly pour the mixture, with continuous stirring, into 234 ml. of 1.1N aqueous sodium bicarbonate. Filter the resultant solid, and extract the filter cake with methylene chloride. Combine the methylene chloride extracts with the methanolic filtrate and remove all solvnt in vacuo. Dissolve the residual solid in ether, wash with water, and dry over anhydrous sodium sulfate. Remove the drying agent, concentrate the solution in vacuo to a volume of 350 ml. and triturate the solid which precipitates. Filter to obtain the analytically pure product, m.p 114°-115° C.

Workup

  1. additionSlowly pour the mixture
  2. filtrationFilter the resultant solid
  3. extractionextract the filter cake with methylene chloride
  4. customremove all solvnt in vacuo
  5. dissolutionDissolve the residual solid in ether
  6. washwash with water
  7. dry with materialdry over anhydrous sodium sulfate
  8. customRemove the drying agent
  9. concentrationconcentrate the solution in vacuo to a volume of 350 ml
  10. customand triturate the solid which
  11. customprecipitates
  12. filtrationFilter
  13. customto obtain the analytically pure product, m.p 114°-115° C.

Sources & evidence

ORD record
ord-67792c8d0a45470cb5dbd026d9e6f53e
Source dataset
uspto-grants-1979_02
Patent number
US04140780

Reaction notes

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