Ethoxyethylamine → N-(2-ethoxyethyl)-3-fluoro-4-nitrobenzamide

HRID 576853Notes

Reaction equation

HRID 576853 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.[CH2:14]([O:16][CH2:17][CH2:18][NH2:19])[CH3:15].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>Cl.C(#N)C>[CH2:14]([O:16][CH2:17][CH2:18][NH:19][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1)[CH3:15]

Participants

8

Reactant 5

HCID 66970EthoxyethylamineHCID 81531DiisopropylethylamineHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 59198706N-(2-ethoxyethyl)-3-fluoro-4-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

3-Fluoro-4-nitrobenzoic acid 5.55 g, 2-ethoxyethylamine 3.15 mL, N,N-diisopropylethylamine 5.23 mL, 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride 8.63 g, 1-hydroxybenzotriazole monohydrate 5.96 g and acetonitrile 77 mL were mixed and stirred for 19 hours. The reaction liquid was poured in diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, saturated aqueous sodium hydrogencarbonate solution and saturated brine, by the order stated, and dried over magnesium sulfate. Distilling the solvent off, 6.86 g of the title compound was obtained.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine, saturated aqueous sodium hydrogencarbonate solution and saturated brine, by the order
  4. dry with materialdried over magnesium sulfate
  5. distillationDistilling the solvent off, 6.86 g of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-b20ee02090e84673b0d51341b5aef9b5
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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