Ammonium Carbonate → (4-Nitrophenyl)methanesulfonamide

HRID 522678Notes

Reaction equation

HRID 522678 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](Cl)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[NH4+:19].[NH4+]>C(#N)C.N>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([NH2:19])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 517111Ammonium CarbonateHCID 2794642(4-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 2755281(4-Nitrophenyl)methanesulfonamideYield 93%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (4-nitrophenyl)methanesulfonyl chloride (4 g, 17 mmol) in acetonitrile (100 mL) was added a solution of ammonium carbonate (3 g, 31.3 mmol) in ammonia (50 mL). The reaction mixture was stirred for 1 h, and TLC indicated the starting material consumed completely. The organic solvent was removed under reduced pressure. Addition of water (10 mL) led to precipitate formation. The solid was collected, washed with water (2×5 mL), and dried to give (4-nitrophenyl)methanesulfonamide (3.4 g, 93%) as a white solid. MS (ES+) C7H8N2O4S requires: 216, found: 217 [M+H]+.

Workup

  1. customconsumed completely
  2. customThe organic solvent was removed under reduced pressure
  3. additionAddition of water (10 mL)
  4. customto precipitate formation
  5. customThe solid was collected
  6. washwashed with water (2×5 mL)
  7. customdried

Sources & evidence

ORD record
ord-682bdb71b5c04a29b771059b4eb53331
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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