Hydrochloric Acid → 2-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606608
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[NH2:17][CH2:18][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+].Cl>O.C(COC)OC.C(N(CC)CC)C>[C:24]([C:22]1[O:23][C:19]([CH2:18][NH:17][C:2]2[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=1)([OH:26])=[O:25]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 221013652,4-Dichloro-5-methanesulfonylbenzoic acidHCID 568075445-(Aminomethyl)furan-2-carboxylic acid hydrochloride

Produkt 1

HCID 215439632-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dichloro-5-methylsulfonylbenzoic acid (3.50 g.; 0.013 mole), 5-aminomethyl-2-furancarboxylic acid hydrochloride (4.83 g.; 0.027 mole), triethylamine (11.5 ml.), and glyme (25 ml.) is heated to 140°-150° C. for 24 hours. Solid sodium bicarbonate (5.0 g.) is added and refluxing is continued for another 24 hours. The mixture is poured into water (150 ml.) and acidified by the addition of 6N hydrochloric acid. The tan solid is collected, washed with water, and dried, 1.20 g., m.p. 269°-272° C. Recrystallization from acetonitrile gives 2-(5-carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid, m.p. 263.5°-265.5° C. (dec.).

Aufarbeitung

  1. temperatureis heated to 140°-150° C. for 24 hours
  2. temperaturerefluxing
  3. customThe tan solid is collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-373033f9ef074426958868561f9e26ad
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953476

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