Potassium Carbonate → HCID 59627719, compound

HRID 1930184Notes

Reaction equation

HRID 1930184 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:19][OH:20]>C(O)C>[OH:20]/[N:19]=[C:9](\[NH2:10])/[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[C:3]([CH3:11])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 578248211259023-88-5

Product 1

HCID 59627719HCID 59627719, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(4-Iodo-3-methylphenyl)acetonitrile (2 g, 7.78 mmol) in ethanol (30 mL) was added dropwise to potassium carbonate (6.67 g, 48.24 mmol) and hydroxylamine hydrochloride (0.541 g, 7.78 mmol) in ethanol (30 mL) at reflux over a period of 5 minutes. The resulting suspension was stirred at reflux for 8 hours. The reaction mixture was allowed to cool overnight and the salts were filtered and washed with DCM (2×50 mL). The filtrate was evaporated to give crude product. The crude product was purified by flash silica chromatography on a combi flash companion 40 g cartridge, elution gradient 0 to 30% MeOH in DCM. Pure fractions were evaporated to dryness to afford (Z)—N′-hydroxy-2-(4-iodo-3-methylphenyl)acetimidamide (1.135 g, 50.3%) as a yellow gum.

Workup

  1. temperatureat reflux over a period of 5 minutes
  2. temperatureat reflux for 8 hours
  3. temperatureto cool overnight
  4. filtrationthe salts were filtered
  5. washwashed with DCM (2×50 mL)
  6. customThe filtrate was evaporated
  7. customto give crude product
  8. customThe crude product was purified by flash silica chromatography on a combi flash companion 40 g cartridge, elution gradient 0 to 30% MeOH in DCM
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2c0c9b7872634e5f812f13c196689925
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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