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

HRID 83871Notes

Reaction equation

HRID 83871 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-1fac26c6380f4ce8a6aa943fe5572fc2
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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