Hydrochloric Acid → HCID 19785553, Verbindung

HRID 256773

Reaktionsgleichung

Reaktionsgleichung von HRID 256773
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:18][CH3:19])[S:13][C:14]=2[C:15](O)=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:38][OH:39].C(N(CC)CC)C.S1C=CN=C1C(O)=O.Cl>C(Cl)Cl.O.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:18][CH3:19])[S:13][C:14]=2[C:15]([NH:38][OH:39])=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

11

Edukt 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 27627331,3-Thiazole-2-carboxylic acidHCID 19785560HCID 19785560, Verbindung

Produkt 1

HCID 19785553HCID 19785553, VerbindungAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cooled and stirred solution of 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid (5.00 g, 14.0 mmoles) and dimethylformamide (1.03 g, 14.1 mmoles) in methylene chloride (200 ml) was added dropwise oxalyl chloride (3.93 g, 31.0 mmoles) and the mixture was stirred for 40 minutes. On the other hand, hydroxylamine hydrochloride (3.91 g, 56.3 mmoles) in water (5 ml) and triethylamine (8.55 g, 84.5 mmoles) were dissolved in tetrahydrofuran (100 ml), and to the mixture was added dropwise the above-mentioned reacted solution of thiazolecarboxylic acid. After stirring for 30 minutes, the reaction mixture was acidified to pH 4 with 1M hydrochloric acid and extracted with methylene chloride. The organic layer was washed with water, dried and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the desired 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarbohydroxamic acid (2.50 g, 6.73 mmoles, 48%) as a light brown amorphous product.

Aufarbeitung

  1. stirringAfter stirring for 30 minutes
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bda1daba9d21467684c7ef2c7cc1ca2f
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258396

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