Ethanolamine → HCID 20508555, Verbindung

HRID 1758779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758779
Cl[CH:2](Cl)[CH3:3].FC1C=CC=CC=1C1C2C=C(N=C=O)C=CC=2N2C(C)=NN=C2CN=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([NH:48][C:49]([NH:51][CH2:52][CH2:53][OH:54])=[O:50])[CH:46]=[CH:47][C:42]=2[N:41]2C=[N:56][N:57]=[C:40]2[CH2:39][N:38]=1.NC1C=CC2N3C(C)=NN=C3CN=C(C3C=CC=CC=3F)C=2C=1.C(=O)([O-])[O-].[Na+].[Na+].C(CN)O>C(#N)C>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([NH:48][C:49]([NH:51][CH2:52][CH2:53][OH:54])=[O:50])[CH:46]=[CH:47][C:42]=2[N:41]2[C:2]([CH3:3])=[N:56][N:57]=[C:40]2[CH2:39][N:38]=1

Komponenten

8

Edukt 6

HCID 700EthanolamineHCID 63651,1-DichloroethaneHCID 10340Sodium CarbonateHCID 20508545HCID 20508545, VerbindungHCID 205085528-amino-6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepineHCID 20508556HCID 20508556, Verbindung

Produkt 1

HCID 20508555HCID 20508555, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A dichloroethane solution of [6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-isocyanate, prepared as described in paragraph (a) of Example 1 from 5 g (16.3 mmol) of 8-amino-6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine, is added dropwise at room temperature while stirring to a suspension of 6.2 g (58.5 mmol) of sodium carbonate in 3 ml (49.8 mmol) of ethanolamine and 40 ml of acetonitrile. After 20 hours, the mixture is partitioned between 500 ml of water and 500 ml of methylene chloride/ethanol (4:1) at 50° C. The separated aqueous phase is treated again in an analogous manner, the combined organic extracts are dried and concentrated in vacuo. Crystallisation of the residue from ethanol yields 1-[6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepin-8-yl]-3-(2-hydroxyethyl)urea of melting point 228°-230° C.

Aufarbeitung

  1. additionis added dropwise at room temperature
  2. customthe mixture is partitioned between 500 ml of water and 500 ml of methylene chloride/ethanol (4:1) at 50° C
  3. additionThe separated aqueous phase is treated again in an analogous manner
  4. customthe combined organic extracts are dried
  5. concentrationconcentrated in vacuo
  6. customCrystallisation of the residue from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f7aba7b1c0f8454db2c45f1650b68ebb
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374773

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