Benzaldehyde → 103899-99-6

HRID 845015Notes

Reaction equation

HRID 845015 reaction equation
[C:1]([NH:4][O:5][CH2:6][C:7]([NH2:9])=[S:8])(=[O:3])[CH3:2].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:1]([N:4]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][C:7](=[S:8])[CH2:6][O:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 20133452HCID 20133452, compound

Product 1

HCID 11971523103899-99-6Yield 52.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

1.48 g (10 millimoles) of alpha-(acetylaminooxy)-thioacetamide are dissolved in a mixture of 10 ml of acetic acid and 1.3 ml of acetic anhydride, thereafter 1.3 ml (13 millimoles) of freshly distilled benzaldehyde and then 0.5 ml of concentrated sulfuric acid are added. The mixture is stirred for 3 hours at room temperature, then 2.8 g of crystalline sodium acetate are added, stirred for 10 minutes, thereafter the solvent is evaporated under vacuum. The residue is dissolved in 30 ml of ethyl acetate, the solution is extracted with 20 ml of water. The organic layer is dried over anhydrous sodium sulfate then evaporated to dryness. The residue is crystallized from ethanol at a temperature of +5° C. 1.25 g (52.9%) of crystalline title product are obtained. M.p.: 172°-174° C. Rf (A)=0.43.

Workup

  1. stirringstirred for 10 minutes
  2. customthe solvent is evaporated under vacuum
  3. dissolutionThe residue is dissolved in 30 ml of ethyl acetate
  4. extractionthe solution is extracted with 20 ml of water
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. customthen evaporated to dryness
  7. customThe residue is crystallized from ethanol at a temperature of +5° C

Sources & evidence

ORD record
ord-78ce386e42d84f95aa4abe877f77f06c
Source dataset
uspto-grants-1988_07
Patent number
US04755510

Reaction notes

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