Tris(2-carboxyethyl)phosphine hydrochloride → 1,2,7-trimethyl-1H-benzimidazol-5-ylamine hydrochloride

HRID 1846439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846439
[N:1]([C:4]1[CH:14]=[C:13]([CH3:15])[C:7]2[N:8]([CH3:12])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=1)=[N+]=[N-].[ClH:16].C(CCP(CCC(O)=O)CCC(O)=O)(O)=O>O1CCOCC1>[ClH:16].[CH3:12][N:8]1[C:7]2[C:13]([CH3:15])=[CH:14][C:4]([NH2:1])=[CH:5][C:6]=2[N:10]=[C:9]1[CH3:11]

Komponenten

4

Edukt 2

HCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 866638995-azido-1,2,7-trimethyl-1H-benzimidazole

Produkt 1

HCID 669781471,2,7-trimethyl-1H-benzimidazol-5-ylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 200 mg (1.00 mmol) 5-azido-1,2,7-trimethyl-1H-benzimidazole, 420 mg (1.50 mmol) tris(2-carboxyethyl)phosphine-hydrochloride, 1.5 mL dioxane and 0.5 mL E-water were combined and the mixture was stirred at RT overnight. Then the reaction mixture was acidified and extracted with EtOAc. The aqueous phase was made alkaline with aqueous sodium hydroxide solution and extracted with DCM. The organic phase was dried on sodium sulphate, filtered and evaporated down. The residue was combined with ethereal hydrochloric acid and the hydrochloride that settled out as precipitate was suction filtered and dried.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionextracted with DCM
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fdcbdc1e35564c5fb8ef3365c1af8bf2
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952014B2

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