Water → 3-Ethynylbenzamide

HRID 2272419Notes

Reaction equation

HRID 2272419 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH2:18])=[O:17])(C)C.O.CCOC(C)=O>CO>[C:12]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH2:18])=[O:17])#[CH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 682830043-((Trimethylsilyl)ethynyl)benzamide

Product 1

HCID 120650003-EthynylbenzamideYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.84 g, 13.3 mmol) was added to a stirred solution of 3-((trimethylsilyl)ethynyl)benzamide (130) (1.45 g, 6.66 mmol) in MeOH (15 mL) at room temperature. The resulting suspension was stirred for 30 minutes then water (100 mL) and EtOAc (100 mL) were added. The resulting precipitate was collected via filtration and after air drying this was suspended in a 1:1 mix of acetone and methanol (15 mL). After sonication the resulting suspension was filtered to give the title compound (I31) (335 mg, 35%) which was used without additional purification.

Workup

  1. filtrationThe resulting precipitate was collected via filtration
  2. customafter air drying
  3. additionmix of acetone and methanol (15 mL)
  4. customAfter sonication the resulting suspension
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-30718685b3e34bd39bc98898850a0041
Source dataset
uspto-grants-2015_09
Patent number
US09120761B2

Reaction notes

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