4-Nitrobenzenesulfonyl chloride → 4-[(4-nitrophenyl)sulfonyl]morpholine

HRID 2408135Notes

Reaction equation

HRID 2408135 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>ClCCl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:25])=[O:24])=[CH:21][CH:22]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 2362694-[(4-nitrophenyl)sulfonyl]morpholineYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of morpholine (5.2 mL, 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 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 4-(4-nitro-benzenesulfonyl)-morpholine (10.0 g, 92.5%) as a white powder: MS (ESI) M+1=273.0.

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-f01beed3dd234d9a982c6feca79fda5f
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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