Triethylamine → alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 1089815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089815
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH:25]=O)[N:24]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.[BH4-].[Na+]>CO>[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH:2][CH2:3][CH:4]([OH:15])[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)[N:24]=1)(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamide

Produkt 1

HCID 14719582alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcoholAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride (2.88 g) and 2-acetamido-4-formyl-thiazole (2.1 g) were suspended in 14 ml methanol, and 1.8 ml triethylamine was added dropwise to this suspension with stirring. The resulting solution was heated under reflux for 30 minutes, and 0.70 g sodium borohydride was added in small portions with stirring under ice cooling. The crystals which separated out were collected by filtration, washed with water and methanol in that order and vacuum-dried, giving 3.55 g of α-[[[(2-acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol (m.p. 204°-206° C.).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 30 minutes
  3. stirringwith stirring under ice cooling
  4. customThe crystals which separated out
  5. filtrationwere collected by filtration
  6. washwashed with water and methanol in that order
  7. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-9c42d12e5f294b639580f9807b912481
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079256

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