Tripropylamine → 2-(2-fluorophenyl)-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)one

HRID 1762075

Reaktionsgleichung

Reaktionsgleichung von HRID 1762075
[C:1](=[O:5])(OC)[NH2:2].N[C:7]1[S:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[C:8]=1[C:16]#[N:17].[F:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([NH:23][NH2:24])=O.C(N(CCC)CCC)CC>COCCO>[F:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]1[N:17]=[C:16]2[N:24]([C:1](=[O:5])[NH:2][C:7]3[S:11][C:10]4[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=4[C:8]=32)[N:23]=1

Komponenten

6

Edukt 4

HCID 7616TripropylamineHCID 11722Methyl CarbamateHCID 783822-Amino-4,5,6,7-tetrahydrobenzo(b)thiophene-3-carbonitrileHCID 1362882-Fluorobenzhydrazide

Produkt 1

HCID 1360582492-(2-fluorophenyl)-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

The methyl carbamate of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo(b)thiophene (7.08 g), 2-fluorobenzhydrazide (4.66 g), 2-methoxyethanol (100 mL) and tri-n-propylamine (3 mL) are refluxed under nitrogen for 19 hours. The mixture is cooled and the precipitate collected. The mother liquor is treated with methanol (100 mL) and refrigerated 24 hours to produce a second crop of solid. The combined material is recrystallized from 2-methoxyethanol and dried 20 hours at 100°/0.01 mm to afford 2-(2-fluorophenyl)-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)one, which decomposes above 316°. The yield is 50%.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. customthe precipitate collected
  3. additionThe mother liquor is treated with methanol (100 mL) and refrigerated 24 hours
  4. customto produce a second crop of solid
  5. customThe combined material is recrystallized from 2-methoxyethanol
  6. customdried 20 hours at 100°/0.01 mm

Quellen und Nachweise

ORD-Eintrag
ord-757ccbfd48df4a8ba2df6af82126b9a5
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831013

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