Sodium Azide → 4-(4-Azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide

HRID 1627356Notes

Reaction equation

HRID 1627356 reaction equation
Br[CH2:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)([CH3:6])[CH3:5].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)([CH3:6])[CH3:5])=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86662251HCID 86662251, compound

Product 1

HCID 866622504-(4-Azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamideYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-bromo-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide (11.3 g, 31.8 mmol) in DMF (50 mL) was added NaN3 (3.1 g, 47.8 mmol, 1.5 eq) at 0° C. After stirring 2 h, the residue was diluted with water and extracted with EtOAc. The combined extracts were washed with 1M HCl and water successively, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography (Hex/EtOAc=4:1 to 2:1) to give 4-(4-azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide (8.0 g, 79% yield) as yellow sticky oil. 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.4 Hz, 1H), 7.43 (s, 1H), 7.29 (d, J=2.2 Hz, 1H), 5.12 (s, 2H), 4.11 (s, 2H), 1.58 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with 1M HCl and water successively
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (Hex/EtOAc=4:1 to 2:1)

Sources & evidence

ORD record
ord-c0852287ce9c47198c7a97d15255b39f
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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