Dimethylformamide → 2-Azido-1-(4-methylsulfanyl-phenyl)-ethanone

HRID 1908252Notes

Reaction equation

HRID 1908252 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].CN(C=O)C.[N-:18]=[N+:19]=[N-:20].[Na+]>CCOC(C)=O>[N:18]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4])=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

Product 1

HCID 161273432-Azido-1-(4-methylsulfanyl-phenyl)-ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

A solution consisting of 2-bromo-1-(4-methylsulfanyl-phenyl)-ethanone (2.00 g, 8.16 mmol) and DMF (7 mL) was cooled to 15° C. and treated portion-wise with sodium azide (583 mg, 8.98 mmol). Once addition was complete, the reaction mixture was stirred for 3 h with gradual warming to rt. The reaction mixture was then diluted with EtOAc (20 mL) and washed with water (25 mL×2), NaHCO3 (satd., 25 mL×2), and brine. The combined organic phases were dried (Na2SO4) and concentrated to dryness to yield the title compound (1.69 g, 100%).

Workup

  1. additionOnce addition
  2. temperaturewith gradual warming to rt
  3. washwashed with water (25 mL×2), NaHCO3 (satd., 25 mL×2), and brine
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6bbde4efda324d1bb92722c4b543e8d2
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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