Dimethylformamide → HCID 178527404, compound

HRID 748755Notes

Reaction equation

HRID 748755 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][C:17]#[N:18])(=[O:15])=[O:14])=[CH:9][CH:8]=1.Cl.C(N(CC)CC)C.[N-:27]=[N+:28]=[N-:29].[Na+]>C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([CH2:16][C:17]2[NH:29][N:28]=[N:27][N:18]=2)(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

Product 1

HCID 178527404HCID 178527404, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To an N,N-dimethylformamide (100 ml) solution of 4-chlorophenylsulfonylacetonitrile (2.81 g, 13.0 mmol) and triethylamine hydrochloride (4.24 g, 65.2 mmol) was added sodium azide (10.8 g, 78.2 mmol) and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was then cooled to room temperature. Ethyl acetate was added and the mixture was washed with a saturated aqueous solution of ammonium chloride. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting solid was washed with diethyl ether and then, collected by filtration, whereby the title compound (2.53 g, 9.78 mmol, 75%) was obtained as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washthe mixture was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-00204baba7174ab18aa309f7883f8ab8
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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