Acetic Acid → HCID 21545740, compound

HRID 1606032Notes

Reaction equation

HRID 1606032 reaction equation
C(O)(=O)C.[CH:5](=O)[CH:6]([CH3:8])[CH3:7].[C:10]1([C:16](=[N:25][OH:26])[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]>N>[C:30]([CH2:29][CH2:28][N:27]1[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N+:25]([O-:26])=[C:5]1[CH:6]([CH3:8])[CH3:7])([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 6561IsobutyraldehydeHCID 6419297Benzil monoxime

Product 1

HCID 21545740HCID 21545740, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

In 200 ml of glacial acetic acid 5.25 ml (0.1 mole) of isobutyraldehyde, 22.5 g (0.1 mole) of benzil monoxime and 8.9 g (0.1 mole) of beta-alanine is heated to reflux temperature for 3 hours. After cooling the mixture is added dropwise under vigorous stirring to one litre of concentrated aqueous ammonia. The solution is extracted with several portions of ether which is discarded. Now pH is adjusted to 7-8 by addition of hydrochloric acid, and further extractions with ether are performed on the resulting slurry. Also this ether is discarded. Finally pH is adjusted to 3 by further addition of hydrochloric acid and the precipitate is filtered off, washed with water and dried. Melting point: 245°-250° C. Thin layer chromatography reveals one spot only.

Workup

  1. temperatureto reflux temperature for 3 hours
  2. temperatureAfter cooling the mixture
  3. additionis added dropwise
  4. extractionThe solution is extracted with several portions of ether which
  5. additionis adjusted to 7-8 by addition of hydrochloric acid, and further extractions with ether
  6. additionis adjusted to 3 by further addition of hydrochloric acid
  7. filtrationthe precipitate is filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-8c1ce9623bcc4b79b00f13aa253443a8
Source dataset
uspto-grants-1976_04
Patent number
US03952005

Reaction notes

Loading…