Ammonia → HCID 10986637, compound

HRID 1975298Notes

Reaction equation

HRID 1975298 reaction equation
C[O:2][C:3](=O)/[C:4](/Cl)=[C:5](\[O:7][CH3:8])/[CH3:6].[OH-].[Na+].[CH:13](=O)[CH:14]([CH3:16])[CH3:15].[NH3:18]>>[CH:13](=[C:6]1/[C:5]([O:7][CH3:8])=[CH:4][C:3](=[O:2])[NH:18]/1)\[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 6561IsobutyraldehydeHCID 14798Sodium Hydroxide2×HCID 5463552HCID 5463552, compound

Product 1

HCID 10986637HCID 10986637, compound

Procedure

120 g of (E)-2-chloro-3-methoxybut-2-enoic acid methyl ester was instilled in 200 ml of concentrated aqueous ammonia solution at 65° to 70° C. with constant passing through of ammonia gas within 3 hours. The reaction mixture was stirred another 1.5 hours at this temperature and then refluxed another 0.5 hour. After cooling to room temperature, 450 ml of 1M sodium hydroxide solution was added and the pH was brought to greater than 13 by the further addition of 33 percent sodium hydroxide solution. Then 50 g of isobutyraldehyde was added and the reaction mixture was heated to 60° C. with stirring for 6 hours. After cooling to room temperature, the precipitated product was filtered off, washed with cold water and dried in a vacuum drying cabinet. The yield of the title compound was 93.2 g (80 percent of theory). The title compound had a melting point of 140.5° to 141.1° C. (from diethyl ether).

Workup

  1. temperaturerefluxed another 0.5 hour
  2. temperaturethe reaction mixture was heated to 60° C.
  3. stirringwith stirring for 6 hours
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitated product was filtered off
  6. washwashed with cold water
  7. customdried in a vacuum
  8. customdrying cabinet

Sources & evidence

ORD record
ord-0f7da661e7a2480abe2007db56fcfabf
Source dataset
uspto-grants-1994_02
Patent number
US05286650

Reaction notes

Loading…