Ammonia → 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester

HRID 447028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447028
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[C:6]([N+:16]([O-])=O)[C:5]=1[S:19][C:20]#[N:21].N>C(O)(=O)C.O.[Fe]>[CH3:1][O:2][C:3]([C:4]1[C:5]2[S:19][C:20]([NH2:21])=[N:16][C:6]=2[CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1)=[O:22]

Komponenten

6

Edukt 2

HCID 222AmmoniaHCID 57813637HCID 57813637, Verbindung

Produkt 1

HCID 578136562-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl esterAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3-Nitro-5-pyridin-3-yl-2-thiocyanato-benzoic acid methyl ester (1.1 g, 3.49 mmol) in glacial acetic acid (23 ml) was treated with iron powder (0.97 g, 17.5 mmol) and stirred at ambient temperature for 16 h. The resultant mixture was diluted with water (200 ml) and made alkaline by the addition of concentrated ammonia solution. The mixture was filtered and the filtrate extracted with ethyl acetate (3×200 ml). The filtered solid was extracted with boiling ethanol (3×250 ml) and the combined organic fractions evaporated to dryness to give 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester as an off-white solid (0.46 g, 46%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate extracted with ethyl acetate (3×200 ml)
  3. extractionThe filtered solid was extracted with boiling ethanol (3×250 ml)
  4. customthe combined organic fractions evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ac634b7a3f444b2bb51836f6a5567c09
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481544B2

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