Chloroacetic Acid → 4-Methylamino-3-chloracetamidobenzoic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

HRID 2288361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288361
[CH2:1]([N:4]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1)[CH2:2][CH3:3].C1(N(CCC(OCC)=O)C(=O)C2C=CC(NCC)=C(N)C=2)C=CC=CC=1.[Cl:49][CH2:50][C:51](O)=[O:52]>O1CCCC1>[CH2:1]([N:4]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH:14][C:51](=[O:52])[CH2:50][Cl:49])[CH:7]=1)[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 184125233-amino-4-ethylaminobenzoic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amideHCID 184125263-Amino-4-methylaminobenzoic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Produkt 1

HCID 184124094-Methylamino-3-chloracetamidobenzoic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1.8 g (5.9 mMol) of 3-amino-4-methylamino-benzoic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)-amide [prepared analogously to 3-amino-4-ethylamino-benzoic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide], 1.1 g (6.8 mMol) of N,N'-carbonyldiimidazole and 0.65 g (6.9 mMol) of chloroacetic acid in 75 ml tetrahydrofuran was stirred for 1 hour at room temperature. Then the solvent was distilled off in vacuo, and the crude product was purified by flash chromatography (silica gel; methylene chloride/ethanol=49:1). Yield: 1.7 g (77% of theory) yellow oil, Rf value: 0.58 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1)

Aufarbeitung

  1. distillationThen the solvent was distilled off in vacuo
  2. customthe crude product was purified by flash chromatography (silica gel; methylene chloride/ethanol=49:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b6612ff2aff4cfdb2cef3e2ddab8afd
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087380

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