Isopropylamine → N-Isopropyl-4-nitrobenzenesulfonamide

HRID 2407987Notes

Reaction equation

HRID 2407987 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13]>ClCCl>[CH:1]([NH:4][S:21]([C:18]1[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=1)(=[O:22])=[O:23])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 2054536N-Isopropyl-4-nitrobenzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of isopropylamine (6.8 mL, 79.6 mmol) and triethylamine (16.6 mL, 119.4 mmol) in dichloromethane (300 mL) was added the solution of 4-nitro-benzenesulfonyl chloride (8.8 g, 39.8 mmol) in dichloromethane (50 mL) at 0° C. The mixture solution stirred at room temperature for 4 h. The mixture solution was stirred at room temperature for 4 h and then washed with brine (50 mL×2) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford N-isopropyl-4-nitro-benzenesulfonamide (9.3 g, 96%) as a white powder: MS (ESI) M+1=245.

Workup

  1. stirringThe mixture solution was stirred at room temperature for 4 h
  2. washwashed with brine (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6244df189267480eb87d9af4f9b89df9
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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