Triethylamine → Methyl 2-[(2,4-dichlorophenyl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate

HRID 1398824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398824
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:14]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=S.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]([CH2:24][CH2:25][CH2:26][OH:27])[C:14]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=[CH:22][C:13]=2[N:12]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632874Methyl 3-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)-2-[(3-hydroxypropyl)amino]benzoate

Produkt 1

HCID 68768601Methyl 2-[(2,4-dichlorophenyl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl 3-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)-2-[(3-hydroxypropyl)amino]benzoate (1.87 g, 4.37 mmol), triethylamine (0.67 mL), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (838 mg, 4.37 mmol) in tetrahydrofuran (15 mL) was stirred at 50° C. for 2 hr. The mixture was diluted with water, concentrated in vacuo, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a pale yellow powder (1.67 g, 4.24 mmol, 97%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-98dd50906c7d4c1eafe44cdf69859404
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

Notizen zur Reaktion

Wird geladen…