Ammonia → HCID 10986637, compound

HRID 1707359Notes

Reaction equation

HRID 1707359 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-d9d930c8d3d045a491bcf44bf562c59a
Source dataset
uspto-grants-1994_10
Patent number
US05352801

Reaction notes

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