4-Acetylmorpholine → Dimethomorph

HRID 2073924

Reaction equation

HRID 2073924 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=O)=[CH:4][CH:3]=1.[C:20]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)(=[O:22])[CH3:21]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 155434-AcetylmorpholineHCID 798751(4-Chlorophenyl)(3,4-dimethoxyphenyl)methanone

Product 1

HCID 86298Dimethomorph

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

4-Chloro-3',4'-dimethoxy benzophenone (6.29 g, 25 mmol), sodium tert.-amylate (5.50 g, 50 mmol), acetyl morpholine (23.90 g, 185 mmol), and anhydrous toluene (50 ml) were stirred under reflux for 8 hours. After cooling, the solution was washed twice with water, dried, and the toluene distilled off on a rotary evaporator. The viscous residue was stirred at 50° C. with diisopropyl ether (40 ml), whereupon the substance solidified. After it had cooled to room temperature, the crude product was crushed, filtered by suction, washed with diisopropyl ether (2×5 ml) and dried.

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureAfter cooling
  3. washthe solution was washed twice with water
  4. customdried
  5. distillationthe toluene distilled off on a rotary evaporator
  6. temperatureAfter it had cooled to room temperature
  7. customthe crude product was crushed
  8. filtrationfiltered by suction
  9. washwashed with diisopropyl ether (2×5 ml)
  10. customdried

Sources & evidence

ORD record
ord-ba156369ae764f25ac4f0d56e1146947
Source dataset
uspto-grants-1990_04
Patent number
US04920222

Linked notes

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