Acetone → HCID 68292992, compound

HRID 1504977Notes

Reaction equation

HRID 1504977 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[S:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][CH2:13][CH2:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.[CH3:22][C:23]([CH3:25])=O>[Cl-].[Cl-].[Zn+2]>[CH3:22][C:23]([NH:21][C:18]1[CH:19]=[N:20][C:15]([CH2:14][CH2:13][CH2:12][C:8]2[S:7][CH:11]=[CH:10][N:9]=2)=[CH:16][CH:17]=1)([CH3:25])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 68292813HCID 68292813, compound

Product 1

HCID 68292992HCID 68292992, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

TMSCN (3.7 mL, 27.9 mmol) was added to a mixture of the compound 139 (2.04 g, 9.3 mmol), acetone (4.1 mL, 55.8 mmol) and ZnCl2 (122 mg, 0.9 mmol) with stirring. The reaction mixture was stirred at 40° C. for 0.5 h, and concentrated in vacuo. The residue was diluted with water, and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 140 (2.6 g, 99%) as a light yellow oil. The crude product was used directly for the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at 40° C. for 0.5 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c331f3389e3845c0be4ae902dfc43cce
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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