1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Fluoro-4-nitrobenzamide

HRID 714909Notes

Reaction equation

HRID 714909 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[Cl-].[NH4+].C([N:18]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 217840942-Fluoro-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-4-nitrobenzoic acid (5.0 g) in N,N-dimethylformamide (100 mL) were added ammonium chloride (7.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (9.5 mL), l-hydroxybenzotriazole (8.3 g) and N,N-diisopropylethylamine (24 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the precipitate was collected by filtration to give the title compound (3.1 g).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8c679557f1914cfa8302e3651004adb4
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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