Diisobutylamine → 4-fluoro-N,N-diisobutyl-3-nitrobenzamide

HRID 883679Notes

Reaction equation

C(N=C=NC(C)C)(C)C.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].[CH2:23]([NH:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:24]([CH3:26])[CH3:25]>C1COCC1>[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:17])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

Participants

Conditions

Temperature: 20 °C

Procedure

Diisopropylcarbodiimide (13.8 ml, 1.2 eq) is added to 4-fluoro-3-nitrobenzoic acid (15 g, 1 eq) in solution in THF (150 ml). The mixture is stirred for 3 hours at a temperature of approximately 20° C. then diisobutylamine (12.9 ml, 1 eq) is added. After stirring for 15 hours at approximately 20° C., the reaction mixture is evaporated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (70 ml). After decantation and extraction, the combined organic phases are washed with salt water, followed by drying over Na2SO4 then evaporating under reduced pressure at 40° C. Purification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2) produces the expected compound in the form of a yellow solid (13.8 g; 63% yield).

Workup

stirringAfter stirring for 15 hours at approximately 20° C.
customthe reaction mixture is evaporated under reduced pressure at 40° C
extractionAfter decantation and extraction
washthe combined organic phases are washed with salt water
dry with materialby drying over Na2SO4
customthen evaporating under reduced pressure at 40° C
customPurification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2)

Sources & evidence

ORD record: ord-5f67905f78734948a28580205e21eda2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236965B2

Reaction notes

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