Toluene → N'-hydroxyhexanimidamide

HRID 470633

Reaction equation

HRID 470633 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[C:9](#[N:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1(C)C=CC=CC=1>C(O)(C)C>[OH:3][NH:2][C:9](=[NH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 12352HexanenitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 3613628N'-hydroxyhexanimidamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.107 g (15.4 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.90 g (22.64 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 1.0 g (10.2 mmol) of hexanenitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After the reaction period, the reaction mixtures was cooled to 25° C. to 30° C., filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue with chased with 5 mL of toluene, to yield the title compound.

Workup

  1. stirringstirred at 80° C. to 85° C. for 3-4 h
  2. customAfter the reaction period
  3. customthe reaction mixtures
  4. temperaturewas cooled to 25° C. to 30° C.
  5. filtrationfiltered
  6. washwashed with 2 mL of isopropyl alcohol
  7. customThe filtrate was collected
  8. distillationdistilled out completely
  9. customto obtain a crude residue

Sources & evidence

ORD record
ord-78c50ea9f043450bbc4ac28dbc99e005
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Linked notes

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