Sodium Hydroxide → HCID 178513382, compound

HRID 1963015Notes

Reaction equation

HRID 1963015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][O:14][C:15]3[C:16]([F:24])=[C:17]([C:20]([F:23])=[CH:21][CH:22]=3)[C:18]#[N:19])[S:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:26][OH:27].[OH-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][O:14][C:15]3[C:16]([F:24])=[C:17]([C:20]([F:23])=[CH:21][CH:22]=3)[C:18]([NH:26][OH:27])=[NH:19])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59591442HCID 59591442, compound

Product 1

HCID 178513382HCID 178513382, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[3-(4-chlorophenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-2,6-difluorobenzonitrile (0.10 g, 2.75 mmol) in EtOH (3 ml) was added hydroxylamine hydrochloride (0.48 g, 6.87 mmol) and NaOH (0.27 g, 6.87 mmol). The resulting reaction mixture was refluxed overnight. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added EtOH and filtered. The filtrate was evaporated in vacuum to get the desired product (0.75 g, 69%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customAfter the completion of the reaction (TLC monitoring)
  4. concentrationthe mixture was concentrated
  5. additionadded EtOH
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuum

Sources & evidence

ORD record
ord-eb6355d3df3340689411f80c27693103
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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