Water → HCID 54505266, compound

HRID 1288275Notes

Reaction equation

HRID 1288275 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:8][OH:9].[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[C:18]([CH:21]=1)[C:19]#[N:20])([CH3:13])([CH3:12])[CH3:11].O>C(O)C>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[C:18]([CH:21]=1)[C:19](=[N:8][OH:9])[NH2:20])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10330141HCID 10330141, compound

Product 1

HCID 54505266HCID 54505266, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium carbonate (57 g.) was added with stirring to a mixture of hydroxylamine hydrochloride (75 g.), 5-tert-butyl-2-methoxybenzonitrile (50 g.) and water (400 ml.) Ethanol (400 ml.) was added, and the mixture was stirred at room temperature for 45 minutes and then heated under reflux for 18 hours. The ethanol was evaporated in vacuo, and the cooled aqueous suspension was extracted three times with diethyl ether. The combined extracts were dried over magnesium sulphate, filtered, and evaporated. The residual glass was triturated with warm diethyl ether, and the solid obtained was filtered off, washed with diethyl ether, and recrystallised from benzene to give 5-tert-butyl-2-methoxybenzamidoxime (48 g.), m.p. 132°-133° C.

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux for 18 hours
  4. customThe ethanol was evaporated in vacuo
  5. extractionthe cooled aqueous suspension was extracted three times with diethyl ether
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residual glass was triturated with warm diethyl ether
  10. customthe solid obtained
  11. filtrationwas filtered off
  12. washwashed with diethyl ether
  13. customrecrystallised from benzene

Sources & evidence

ORD record
ord-b8ea7304747140b5899e96755de3c7b8
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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