Tert-Butylamine → N-[4-(tert-butylsulfamoyl)phenyl]acetamide

HRID 446154Notes

Reaction equation

HRID 446154 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>COCCOC>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 8481N-Acetylsulfanilyl chloride

Product 1

HCID 668309N-[4-(tert-butylsulfamoyl)phenyl]acetamideYield 68.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of 4-acetylaminobenzenesulfonyl chloride (10 g, 43 mmol) in DME (103 mL) is added, at 0° C., tert-butylamine (9 mL, 86 mmol) in DME (103 mL). Next, the reaction mixture is stirred for 4 h at reflux. The solvent is removed and CHCl3 is added. The resulting suspension is filtered and the solid is washed with CHCl3, H2O and Et2O. The solid obtained is dried in vacuo to give 8.0 g of the product as a white solid (yield: 68%).

Workup

  1. additionis added, at 0° C.
  2. temperatureat reflux
  3. customThe solvent is removed
  4. additionCHCl3 is added
  5. filtrationThe resulting suspension is filtered
  6. washthe solid is washed with CHCl3, H2O and Et2O
  7. customThe solid obtained
  8. customis dried in vacuo

Sources & evidence

ORD record
ord-a0b689c660f54a41be488785b6180628
Source dataset
uspto-grants-2013_07
Patent number
US08476456B2

Reaction notes

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