Methanol → N-ethyl-4-nitrobenzamide

HRID 376493Notes

Reaction equation

HRID 376493 reaction equation
Cl.[NH2:2][OH:3].[C:4]([O-])(=O)[CH3:5].[Na+].[C:9]([NH2:17])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[OH:19]>>[CH2:4]([NH:17][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][C:13]([N+:2]([O-:19])=[O:3])=[CH:12][CH:11]=1)[CH3:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 2331BenzamideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 347925N-ethyl-4-nitrobenzamide

Conditions

Temperature
45 °C

Procedure

The reaction medium is reheated to 20° C. and 55 kg of methanol are then added. 24 kg (345 mol) of hydroxylamine hydrochloride are subsequently added and the reaction medium is heated to 45° C. 17 kg (207 mol) of sodium acetate are added and the heating is continued for 6 hours. The major portion of the solvents is removed by distillation under reduced pressure. The yellow-coloured reaction medium becomes viscous. 175 kg of distilled water are added at 65° C. The amidoxime gradually precipitates. The reaction medium is coloured orange/ochre. Stirring is continued at 45° C. for 1 hour. Filtering, rinsing with water and then drying results in 38.3 kg of the expected amidoxime, which is 98% pure as determined by TLC, signifying a yield of 77% based on the starting benzamide.

Workup

  1. customis reheated to 20° C.
  2. customThe major portion of the solvents is removed by distillation under reduced pressure
  3. addition175 kg of distilled water are added at 65° C
  4. customThe amidoxime gradually precipitates
  5. waitis continued at 45° C. for 1 hour
  6. filtrationFiltering
  7. washrinsing with water
  8. customdrying
  9. customresults in 38.3 kg of the expected amidoxime

Sources & evidence

ORD record
ord-439effd2923a4fe3ae52408b124a56f4
Source dataset
uspto-grants-2000_02
Patent number
US06020498

Reaction notes

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