Sodium sulfate decahydrate → 3-Chloro-5-(hydroxymethyl)benzamide

HRID 1432064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432064
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7](OC)=[O:8])(=[O:3])[NH2:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:14][C:12]1[CH:13]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:1]([NH2:2])=[O:3]

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

Produkt 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamideAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step N4. To above methyl 3-carbamoyl-5-chlorobenzoate (˜9.3 mmol) in dry THF (100 mL) was added lithium aluminum hydride (1 g, 26.3 mmol) in portions. The mixture was stirred for 4 hours, then treated with sodium sulfate decahydrate (8.5 g, 26.3 mmol) for 30 min. The solid was filtered off and washed with THF for three times. The solvent was removed under vacuum and resulting residue was purified by column with DCM, then MeOH/DCM (5/95) to give 3-chloro-5-(hydroxymethyl)benzamide (13, 0.7 g, 40%).

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. washwashed with THF for three times
  3. customThe solvent was removed under vacuum
  4. customresulting residue
  5. customwas purified by column with DCM

Quellen und Nachweise

ORD-Eintrag
ord-b345ff0a8ab64868bf750c4c9695934b
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612069B2

Notizen zur Reaktion

Wird geladen…