Hydroxyamine hydrochloride → HCID 86659950, compound

HRID 1804521Notes

Reaction equation

HRID 1804521 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.Cl.[NH2:15][OH:16].C(=O)(O)[O-].[Na+]>CO>[OH:16][N:15]=[C:6]([NH2:7])[C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=1[C:10]([F:13])([F:11])[F:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27755974-Methyl-2-(trifluoromethyl)benzonitrile

Product 1

HCID 86659950HCID 86659950, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An oven-dried 20 mL reaction vial containing a stir bar was cooled under a stream of dry nitrogen. The vial was charged with 4-methyl-2-(trifluoromethyl)benzonitrile (1000 mg, 5.40 mmol), hydroxylamine hydrochloride (469 mg, 6.75 mmol), sodium bicarbonate (681 mg, 8.10 mmol), and methanol (6 mL). The vial was flushed with nitrogen, sealed, stirred at room temperature for 30 minutes, and then placed in a sand bath set to 75° C. and stirred overnight. The crude reaction material was purified by reverse phase preparative HPLC. The collected product fractions were evaporated under vacuum to afford N′-hydroxy-4-methyl-2-(trifluoromethyl)benzimidamide (0.54 g, 2.45 mmol, 45% yield). MS M+1=219.0.

Workup

  1. customAn oven-dried 20 mL reaction
  2. additionvial containing a stir bar
  3. temperaturewas cooled under a stream of dry nitrogen
  4. customThe vial was flushed with nitrogen
  5. customsealed
  6. customplaced in a sand bath
  7. customset to 75° C.
  8. stirringstirred overnight
  9. customThe crude reaction material
  10. customwas purified by reverse phase preparative HPLC
  11. customThe collected product fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-2c8cbcfb06914b3baf4cd253207fcdfb
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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