Ammonia → HCID 12619215, compound

HRID 1975302Notes

Reaction equation

HRID 1975302 reaction equation
[NH3:1].C[O:3][C:4](=O)/[C:5](/Cl)=[C:6](\[O:8]C)/[CH3:7].[OH-].[Na+].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O>[CH:14](=[C:7]1/[C:6](=[O:8])[CH2:5][C:4](=[O:3])[NH:1]/1)\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5463552HCID 5463552, compound

Product 1

HCID 12619215HCID 12619215, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

133 g of concentrated aqueous ammonia solution was heated to 65° to 70° C. 75 g of (E)-2-chloro-3-methoxybut-2-enoic acid methyl ester was instilled for 3 hours with constant passing through of ammonia gas. The mixture was stirred another 45 minutes at this temperature, heated 30 minutes to reflux temperature and then cooled to room temperature. After the addition of 300 ml of water and 50 ml of 33 percent sodium hydroxide solution, 46.4 g of benzaldehyde was added. The mixture was heated for 6 hours at 60° C. under stirring and then cooled to room temperature. Then 688 ml of concentrated hydrochloric acid was added and the reaction mixture was stirred for 22 hours at 40° C. After cooling to room temperature, the yellow product was filtered off, washed with cold water and dried in a vacuum drying cabinet. The yield of the title compound was 74.66 g (88 percent of theory). The title compound had a melting point of 186° to 187° C. (THF/hexane).

Workup

  1. temperatureheated 30 minutes
  2. temperatureto reflux temperature
  3. additionwas added
  4. temperatureThe mixture was heated for 6 hours at 60° C.
  5. stirringunder stirring
  6. temperaturecooled to room temperature
  7. stirringthe reaction mixture was stirred for 22 hours at 40° C
  8. temperatureAfter cooling to room temperature
  9. filtrationthe yellow product was filtered off
  10. washwashed with cold water
  11. customdried in a vacuum
  12. customdrying cabinet

Sources & evidence

ORD record
ord-f999b4a6c37b4e13a760d3dd6001f9d2
Source dataset
uspto-grants-1994_02
Patent number
US05286650

Reaction notes

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