Sodium hydride → HCID 9875780, compound

HRID 1358753Notes

Reaction equation

HRID 1358753 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:14]=[C:13]([OH:15])[C:12]([CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:11][C:9]=2[OH:10])[CH2:3][CH2:2]1.[H-].[Na+].[N+:25]([C:28]1[CH:33]=[C:32]([S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])[CH:31]=[CH:30][C:29]=1Cl)([O-:27])=[O:26]>C1COCC1>[N:17]1([CH2:16][C:12]2[C:13]([O:15][C:29]3[CH:30]=[CH:31][C:32]([S:34]([C:37]([F:39])([F:40])[F:38])(=[O:36])=[O:35])=[CH:33][C:28]=3[N+:25]([O-:27])=[O:26])=[CH:14][C:8]([CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[C:9]([O:10][C:29]3[CH:30]=[CH:31][C:32]([S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[CH:33][C:28]=3[N+:25]([O-:27])=[O:26])[CH:11]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2293662,5-Bis[(morpholin-4-yl)methyl]benzene-1,4-diolHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Product 1

HCID 9875780HCID 9875780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-bis-(morpholinomethyl)-hydroquinone (100 mg, 0.324 mmol) in THF was added sodium hydride (26 mg of 60% dispersion in mineral oil) followed by 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (188 mg, 0.648 mmol). The mixture was stirred at room temperature for overnight. The reaction was extracted with ethyl acetate, the organic layer was washed with water and brine, dried, concentrated and purified to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.81 (d, J=2.2 Hz, 2H), 8.23 (m, 2H), 7.60 (s, 2H), 7.27 (m, 2H), 3.4 (m, 4H, 2×CH2), 3.06 (m, 8H, 4×CH2), 2.18 (m, 8H, 4×CH2). MS 815 [M++1].

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-b06b5ba2344940abb0a9494d805fe83e
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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