Benzenesulfonyl chloride → HCID 12297945, Verbindung

HRID 1730644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1730644
[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[C:8]([CH3:17])[C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[Na+]>[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[C:8]([CH3:17])[C:3]=1[C:4]([NH:6][NH:7][S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25])=[O:5]

Komponenten

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 12297944HCID 12297944, Verbindung

Produkt 1

HCID 12297945HCID 12297945, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-acetamido-4,6-dimethylnicotinic acid hydrazide (34.4 g., 0.145 mole) in 1N sodium hydroxide solution (348 ml.) is added at ambient temperature and with vigorous stirring, benzenesulfonyl chloride (31.1 g., 0.16 mole) in one portion. After about three-quarters of an hour the acid chloride disappears; the maximum temperature attained by the reaction mixture, 36° C. The product is precipitated by pouring the reaction mixture into a stirred solution of acetic acid (8.3 ml.) in water (250 ml.). It is collected, slurried with water (150 ml.), refiltered and dried affording 49.52 g. (90%) of crude product, m.p. 216°-218° C. with gas evolution. Following purification by dissolving in hot (100° C.) dimethylformamide, filtering, and diluting with methanol (1 part) and water (3 parts) the product melts at 233°-234° C. (dec.).

Aufarbeitung

  1. customabout three-quarters of an hour
  2. customattained by the reaction mixture, 36° C
  3. customThe product is precipitated
  4. additionby pouring the reaction mixture into a stirred solution of acetic acid (8.3 ml.) in water (250 ml.)
  5. customIt is collected
  6. customdried
  7. customaffording 49.52 g
  8. custompurification
  9. dissolutionby dissolving in hot (100° C.) dimethylformamide
  10. filtrationfiltering
  11. additiondiluting with methanol (1 part) and water (3 parts) the product melts at 233°-234° C. (dec.)

Quellen und Nachweise

ORD-Eintrag
ord-298a4fe00c6146d5b8755cdf762e77a4
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03993656

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