Water → 1,1-Dimethylethyl N-[4-[(hydroxyimino)methyl]phenyl]carbamate

HRID 1352512Notes

Reaction equation

HRID 1352512 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+].O>C(O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[N:18][OH:19])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2771821tert-Butyl (4-formylphenyl)carbamate

Product 1

HCID 851578641,1-Dimethylethyl N-[4-[(hydroxyimino)methyl]phenyl]carbamateYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-formylphenyl)carbamic acid tert-butyl ester (1.0 g), hydroxylamine hydrochloride (0.31 g), and sodium acetate (0.37 g) in ethanol (8.5 mL)/water(1.5 mL) is heated at reflux temperature for 1 hour. The mixture is cooled to ambient temperature and partitioned between diethyl ether and water. The aqueous layer is back-extracted with diethyl ether and the combined organic extracts are washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.8 g pure white solid as the product. MS: m/z 237 (M+H)+.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. custompartitioned between diethyl ether and water
  3. extractionThe aqueous layer is back-extracted with diethyl ether
  4. washthe combined organic extracts are washed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c21684ba0ecf4968b61df347c6ca9ea1
Source dataset
uspto-grants-2007_05
Patent number
US07220768B2

Reaction notes

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