Benzyl Bromide → 3-Benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid

HRID 918681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918681
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:15](=[O:18])(=[O:17])[NH2:16])[C:10]=1[NH:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=[O:6].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:15](=[O:18])(=[O:17])[NH2:16])[C:10]=1[NH:11][CH:12]([CH3:13])[CH3:14])[C:5]([OH:7])=[O:6])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 215059903-Amino-4-isopropylamino-5-sulphamyl-benzoic acid

Produkt 1

HCID 215060283-Benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-4-isopropylamino-5-sulphamyl-benzoic acid (2.62 g), benzyl bromide (4.28 g), and anhydrous ethanol (25 ml) was refluxed for 24 hours. The reaction mixture was evaporated in vacuo. 1N sodium hydroxide (30 ml) was added, and the mixture was heated on a steam bath for 1 hour. After cooling and extracting with diethyl ether, the aqueous layer was adjusted to a pH of 3 by addition of 4N hydrochloric acid. The precipitated 3-benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid was collected by suction and recrystallized from aqueous ethanol. The melting point was 233°-234°C.

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. addition1N sodium hydroxide (30 ml) was added
  4. temperaturethe mixture was heated on a steam bath for 1 hour
  5. temperatureAfter cooling
  6. extractionextracting with diethyl ether
  7. additionthe aqueous layer was adjusted to a pH of 3 by addition of 4N hydrochloric acid
  8. customThe precipitated 3-benzylamino-4-isopropylamino-5-sulphamyl-benzoic acid was collected by suction
  9. customrecrystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-38161ddd06234e339e2b00e347a1e3bc
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971819

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