Potassium Carbonate → HCID 178484441, compound

HRID 2172677Notes

Reaction equation

HRID 2172677 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:21][OH:22]>CCO.CCOC(C)=O>[OH:22][NH:21][C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=[CH:5][CH:4]=1)=[NH:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 162277964-Cyano-N,N-dimethylbenzamide

Product 1

HCID 178484441HCID 178484441, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-cyano-N,N-dimethylbenzamide (200 mg, 1.148 mmol), potassium carbonate (952 mg, 6.89 mmol) and hydroxylamine hydrochloride (479 mg, 6.89 mmol) were dissolved in EtOH (11.4 mL). The reaction mixture was stirred at 80° C. for 25 h. The mixture was diluted with EtOAc (50 mL), washed with water (10 mL), water phase extracted with EtOAc (20 mL). Combined organic phases were washed with brine (10 mL) and dried over sodium sulfate. The solvent was removed to give 188 mg of white crystalline needles. The crude material was used without further purification.

Workup

  1. washwashed with water (10 mL), water phase
  2. extractionextracted with EtOAc (20 mL)
  3. washCombined organic phases were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-5d180c150ed044609ff387b770a67238
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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