Triethylamine → [5-(2,4-Dichlorophenyl)-[1,3,4]thiadiazol-2-yl]carbamic acid 1-methyl-1H-benzimidazol-5-ylmethyl ester

HRID 1498954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1498954
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([NH2:14])=[N:11][N:10]=1.[C:15](Cl)(=O)[O:16]C1C=CC=CC=1.C(N(CC)CC)C.[CH3:32][N:33]1[C:37]2[CH:38]=[CH:39][C:40]([CH2:42][OH:43])=[CH:41][C:36]=2[N:35]=[CH:34]1.N12CCCN=C1CCCCC2>O1CCCC1>[CH3:32][N:33]1[C:37]2[CH:38]=[CH:39][C:40]([CH2:42][O:43][C:15](=[O:16])[NH:14][C:12]3[S:13][C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])=[N:10][N:11]=3)=[CH:41][C:36]=2[N:35]=[CH:34]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1826385-(2,4-Dichlorophenyl)-1,3,4-thiadiazol-2-amineHCID 14518388(1-methyl-1H-benzo[d]imidazol-5-yl)methanol

Produkt 1

HCID 68642019[5-(2,4-Dichlorophenyl)-[1,3,4]thiadiazol-2-yl]carbamic acid 1-methyl-1H-benzimidazol-5-ylmethyl esterAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In tetrahydrofuran (20 ml), 5-(2,4-dichlorophenyl)-[1,3,4]thiadiazol-2-ylamine (80 mg, 0.33 mmol) was suspended, and phenyl chlorocarbonate (56 mg, 0.36 mmol) and triethylamine (36 mg, 0.36 mmol) were added thereto. The mixture was stirred at a room temperature for one hour. To the mixture, (1-methyl-1H-benzimidazol-5-yl)methanol (63 mg, 0.39 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (60 mg, 0.39 mmol) were added, and the resulting mixture was heated and stirred for one hour. After the resulting mixture was allowed to cool, the precipitate was washed with a small quantity of chloroform to give the title compound (20 mg, 14%) as a light-brown substance.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. stirringstirred for one hour
  3. temperatureto cool
  4. washthe precipitate was washed with a small quantity of chloroform

Quellen und Nachweise

ORD-Eintrag
ord-af73bd825c0b4639b9328ad6c5979a27
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200008B2

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