Benzaldehyde → HCID 66880160, compound

HRID 1893522Notes

Reaction equation

HRID 1893522 reaction equation
C(=[N:8][N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH2:11][CH2:10]1)C1C=CC=CC=1.Cl.C(=O)C1C=CC=CC=1>>[N+:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[S:15]([N:12]1[CH2:11][CH2:10][N:9]([NH2:8])[CH2:14][CH2:13]1)(=[O:17])=[O:16])([O-:26])=[O:25]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 66880812HCID 66880812, compound

Product 1

HCID 66880160HCID 66880160, compoundYield 96%

Procedure

To the compound (6.61 g, 17.67 mmol) obtained in step B was added 1N hydrochloric acid, and generated benzaldehyde was evaporated by azeotropic distillation in a flask mounted with Dean-Stark water removing apparatus (Dean-Stark trap) for 6 hr. The reaction mixture was cooled, washed with diethyl ether, and the aqueous layer was alkalified with potassium carbonate. The layer was extracted twice with ethyl acetate (150 ml), and the organic layer was combined. The mixture was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solvent was concentrated under reduced pressure to give the title compound (4.85 g, yield 96%) as a yellow oil.

Workup

  1. customwas evaporated by azeotropic distillation in a flask
  2. temperatureThe reaction mixture was cooled
  3. washwashed with diethyl ether
  4. extractionThe layer was extracted twice with ethyl acetate (150 ml)
  5. washThe mixture was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-943e8ba8b71947b882b5784a92156045
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

Loading…