Acetic Acid → Tert-butyl 2-hydroxyimino-3-phenyliminobutyrate

HRID 1088047Notes

Reaction equation

HRID 1088047 reaction equation
[OH:1][N:2]=[C:3]([C:11](=O)[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.O>C1C=CC=CC=1>[OH:1][N:2]=[C:3]([C:11](=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6115AnilineHCID 178468384tert-butyl 2-hydroxyimino-3-oxobutanoate

Product 1

HCID 136404523Tert-butyl 2-hydroxyimino-3-phenyliminobutyrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of tert-butyl 2-hydroxyimino-3-oxobutyrate (130 g), aniline (76 ml) and acetic acid (14 ml) in benzene (1.2 l) was refluxed with Dean Stark water separator for 5 hours. The resulting solution was cooled and washed with 5% aqueous sodium bicarbonate solution and water. After being dried over magnesium sulfate, the organic solvent was evaporated in vacuo. The residue was triturated with a mixture of n-hexane (300 ml) and diisopropyl ether (100 ml). The precipitate was collected by filtration, washed with n-hexane to give tert-butyl 2-hydroxyimino-3-phenyliminobutyrate (71.2 g).

Workup

  1. temperatureThe resulting solution was cooled
  2. washwashed with 5% aqueous sodium bicarbonate solution and water
  3. dry with materialAfter being dried over magnesium sulfate
  4. customthe organic solvent was evaporated in vacuo
  5. customThe residue was triturated with a mixture of n-hexane (300 ml) and diisopropyl ether (100 ml)
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with n-hexane

Sources & evidence

ORD record
ord-8be848048044461db82d7907f626bfa5
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

Loading…