Methanol → N-ethyl-4-nitrobenzenesulfonamide

HRID 578652Notes

Reaction equation

HRID 578652 reaction equation
[CH2:1]([NH2:3])[CH3:2].CO.[S:6](Cl)([C:9]1[CH:17]=[CH:16][C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=1)(=[O:8])=[O:7]>O>[CH2:1]([NH:3][S:6]([C:9]1[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[CH:16][CH:17]=1)(=[O:7])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 232621N-ethyl-4-nitrobenzenesulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 40-mL vial with magnetic stir bar at 25° C. was added the Ethylamine solution (0.91 g, 20 mmol, 1.3 mL, 70% w/v in water, 4.5 eq.) and methanol (5 mL). The reaction vial was cooled to 0° C. The Nosyl chloride (1.0 g, 4.5 mmol, 1 eq.) was added portion-wise keeping the temperature between 0-5° C. and stirring continued ×15 min. after addition was complete. Water (10 mL) was then added. A precipitate began to form immediately. Stirring was continued at 0° C.×30 minutes. The material was collected by filtration, rinsed with water, and dried thoroughly in vacuo to afford 827 mg (79% yield). LCMS (ESI) 231 (M+H); 229 (M−H).

Workup

  1. customThe reaction
  2. custombetween 0-5° C.
  3. custom×15 min.
  4. additionafter addition
  5. customto form immediately
  6. stirringStirring
  7. customwas continued at 0° C.
  8. custom×30 minutes
  9. filtrationThe material was collected by filtration
  10. washrinsed with water
  11. customdried thoroughly in vacuo
  12. customto afford 827 mg (79% yield)

Sources & evidence

ORD record
ord-827336aac49f4e109fb652162b669f93
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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