Morpholine → HCID 796972, compound

HRID 1977955Notes

Reaction equation

HRID 1977955 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][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15]>ClCCl>[N:1]1([S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])(=[O:24])=[O:25])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 796972HCID 796972, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of morpholine (1.91 g, 22 mmol and triethylamine (2.2 g, 22 mmol) in dichloromethane (100 mL) at 0° C. was added 2-nitrobenzenesulfonyl chloride (4.42 g, 20 mmol). The mixture was stirred for 4 h and then additional dichloromethane (100 mL) was added. The dichloromethane solution was washed with saturated NaHCO3 (2×50 mL), 10% HCl (2×50 mL) and brine (50 mL) and dried over Na2SO4. Evaporating the solvent in vacuo gave the title compound as a yellow solid (5.3 g, 97%). 1H-NMR (300 MHz, CDCl3) δ7.97 (d, J=7.3 Hz, 1H), 7.62-7.77 (m, 3H), 3.75 (t, J=4.7 Hz, 4H), 3.30 (t, J=4.8 Hz, 4H).

Workup

  1. washThe dichloromethane solution was washed with saturated NaHCO3 (2×50 mL), 10% HCl (2×50 mL) and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. customEvaporating the solvent in vacuo

Sources & evidence

ORD record
ord-66d6844b87b34bcf87f6345393ef90e8
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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