4-Nitrobenzenesulfonyl chloride → HCID 22326749, compound

HRID 2407992Notes

Reaction equation

HRID 2407992 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>ClCCl>[CH:1]1([NH:5][S:22]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=2)(=[O:23])=[O:24])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 75645Cyclobutylamine

Product 1

HCID 22326749HCID 22326749, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of cyclobutylamine (4.3 g, 59.7 mmol) and triethylamine (11.2 mL, 79.6 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 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-cyclobutyl-4-nitro-benzenesulfonamide (9.4 g, 92.5%) as a white powder: MS (ESI) M+1=257.1.

Workup

  1. washwashed with brine (50 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c518352accca432ebd2375526e40bd93
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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