Sodium hydride → HCID 9939538, compound

HRID 1358757Notes

Reaction equation

HRID 1358757 reaction equation
C([C:3]1[C:8]([C:9]([NH2:11])=[O:10])=[C:7](CC)[C:6]([OH:14])=[CH:5][C:4]=1[OH:15])C.[H-].[Na+].[N+:18]([C:21]1[CH:26]=[C:25]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=1Cl)([O-:20])=[O:19]>C1COCC1>[N+:18]([C:21]1[CH:26]=[C:25]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=1[O:14][C:6]1[CH:7]=[C:8]([CH:3]=[C:4]([O:15][C:22]2[CH:23]=[CH:24][C:25]([S:27]([C:30]([F:32])([F:33])[F:31])(=[O:29])=[O:28])=[CH:26][C:21]=2[N+:18]([O-:20])=[O:19])[CH:5]=1)[C:9]([NH2:11])=[O:10])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 131723993HCID 131723993, compound

Product 1

HCID 9939538HCID 9939538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 3,5-dihydroxybenzamide (100 mg, 0.6553 mmol) in THF was added sodium hydride (60 mg of 60% dispersion in mineral oil) followed by 2-nitro-4-(trifluoromethylsulfonyl) chlorobenzene (378 mg, 1.306 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 11.32 (br s, 1H, NH), 10.58 (br s, 1H, NH), 8.78 (d, J=2.2 Hz, 1H), 8.57 (br s, 1H), 8.47 (br d, 1H), 8.33 (dd, J=2.2 & 8.8 Hz, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.40 (d, J=9.3 Hz, 1H), 7.35 (m, 2H), 7.01 (br s, 1H).

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-7d633d29ab454e658a4085133d6c27a6
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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