Water → N-[3-(Azidomethyl)-5-(1-methylethenyl)phenyl]-N-methylmethanesulfonamide

HRID 2071056Notes

Reaction equation

HRID 2071056 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1)=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 68669918HCID 68669918, compound

Product 1

HCID 86647428N-[3-(Azidomethyl)-5-(1-methylethenyl)phenyl]-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of crude N-(3-(chloromethyl)-5-(prop-1-en-2-yl)phenyl)-N-methylmethanesulfonamide and 91.2 mg (1.40 mmol) of NaN3 in 4 mL of DMF was stirred at 70° C. for about 3 h. Water and EtOAc were added, and the organic layer was washed with water (2×) and then brine. The aqueous layer was extracted with EtOAc, and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography provided 88.4 mg of N-(3-(azidomethyl)-5-(prop-1-en-2-yl)phenyl)-N-methylmethanesulfonamide as a mixture.

Workup

  1. washthe organic layer was washed with water (2×)
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-42c8471bab354fd5b3feecebbf425582
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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