Ethanol → 2-chloro-6-fluoro-N'-hydroxybenzenecarboximidamide

HRID 2228858Notes

Reaction equation

HRID 2228858 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4](=[N:12][OH:13])[NH2:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 695872-Chloro-6-fluorobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 46234272-chloro-6-fluoro-N'-hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of 15.6 g of 2-chloro-6-fluorobenzonitrile, 9.0 g of hydroxylamine hydrochloride, 7.4 g of sodium carbonate, 50 ml of ethanol and 15 ml of water was stirred at 70-75° C. for 16 h. The solvent was evaporated and the residue was stirred with tertbutyl methyl ether, and the filtrate afforded, after evaporation of the solvent, 17.6 g of the desired product of m.p. 115-120° C.

Workup

  1. customThe solvent was evaporated
  2. stirringthe residue was stirred with tertbutyl methyl ether
  3. customthe filtrate afforded
  4. customafter evaporation of the solvent, 17.6 g of the desired product of m.p. 115-120° C.

Sources & evidence

ORD record
ord-5be28282c74240769217d730973e239e
Source dataset
uspto-grants-2002_07
Patent number
US06417398B1

Reaction notes

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