Sodium hydride → HCID 17981667, compound

HRID 2252059Notes

Reaction equation

[H-].[Na+].[CH:3]([S:6]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:8])=[O:7])([CH3:5])[CH3:4].F[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28]>O1CCCC1>[CH:3]([S:6]([N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])(=[O:8])=[O:7])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Suspend sodium hydride (60% in mineral oil, 0.85 g, 21.2 mmol) in tetrahydrofuran (100 mL). Add 1 N-[isopropylsulfonyl]-4-methoxy-benzylamine (4.73 g, 19.45 mmol) in tetrahydrofuran (400 mL) and heat to 70° C. Stir 10 minutes, then add 2,4-difluoronitrobenzene (3.2 mL, 29.2 mmol) in one portion and stir 18 hours at 70° C. Cool to ambient temperature and remove solvents under reduced pressure. Dissolve in ethyl acetate and wash twice with 1 N HCl aq., three times with saturated sodium hydrogen carbonate, saturated sodium carbonate, 1 N HCl aq., dry magnesium sulfate, filter and remove solvents under reduced pressure. Purify on silica gel with dichloromethane/hexane mixtures to give 5.395 g (72%) of the title compound.

Workup

temperatureCool to ambient temperature
customremove solvents under reduced pressure
dissolutionDissolve in ethyl acetate
washwash twice with 1 N HCl aq., three times with saturated sodium hydrogen carbonate, saturated sodium carbonate, 1 N HCl aq., dry magnesium sulfate
filtrationfilter
customremove solvents under reduced pressure
customPurify on silica gel with dichloromethane/hexane

Sources & evidence

ORD record: ord-89cb58b53b644ec2bb41fbbf1b0c9f5c
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320995B2

Reaction notes

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