Diisoamylamine → 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

HRID 2063504Notes

Reaction equation

HRID 2063504 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27]([OH:29])=O.[CH2:36]([NH:41][CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:37][CH:38]([CH3:40])[CH3:39]>C1COCC1.C(Cl)(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27]([N:41]([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:36][CH2:37][CH:38]([CH3:39])[CH3:40])=[O:29]

Participants

7

Reactant 4

HCID 10988DiisoamylamineHCID 757711-HydroxybenzotriazoleHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamideYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1-hydroxybenzotriazole (HOBt) (8 g, 1.1 eq) in solution in THF (60 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (11.4 g, 1.1 eq) in solution in chloroform (60 ml) are added successively to 3-fluoro-4-nitrobenzoic acid (10 g, 1 eq) in solution in anhydrous THF (60 ml). The mixture is stirred for 2 hours at a temperature of approximately 20° C. then diisoamylamine (12.2 ml, 1.1 eq) is added. After stirring for 4 hours at a temperature of approximately 20° C., the reaction mixture is concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (300 ml) and water (100 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent:heptane 100% to heptane/ethyl acetate 70:30) produces the expected compound (12.36 g; 71% yield).

Workup

  1. stirringAfter stirring for 4 hours at a temperature of approximately 20° C.
  2. concentrationthe reaction mixture is concentrated under reduced pressure at 40° C
  3. extractionAfter decantation and extractions
  4. washthe combined organic phases are washed with salt water
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated under reduced pressure at 40° C
  7. customPurification by flash chromatography on silica gel (eluent:heptane 100% to heptane/ethyl acetate 70:30)

Sources & evidence

ORD record
ord-fdcae4f2dd94448a9a6f38e6ca9c3bbe
Source dataset
uspto-grants-2012_10
Patent number
US08288395B2

Reaction notes

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