Ethanol → 4-chloro-N'-hydroxybenzenecarboximidamide

HRID 1051401Notes

Reaction equation

HRID 1051401 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[NH2:11][OH:12].CCO.CCN(C(C)C)C(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[N:11][OH:12])[NH2:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 121634-ChlorobenzonitrileHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2246504-chloro-N'-hydroxybenzenecarboximidamideYield 64.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 mL round-bottomed flask, 4-chlorobenzonitrile (2 g, 14.5 mmol) and hydroxylamine hydrochloride (1.00 g, 14.5 mmol) were combined with EtOH (20 ml) to give a colorless solution. DIEA (2.82 g, 3.81 ml, 21.8 mmol) was added and the reaction mixture was heated at 100° C. and stirred for 6 h. The crude reaction mixture was diluted with ethyl acetate (100 ml) and filtered. The solid was collected, washed with ethyl acetate and dried to afford 1.6 g (64%) of 4-chloro-N′-hydroxybenzimidamide as a white solid.

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. filtrationfiltered
  4. customThe solid was collected
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-5b7d8ae441774c878eec5f829aa37735
Source dataset
uspto-grants-2016_07
Patent number
US09388172B2

Reaction notes

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