Acetic Acid → 6-Chloro-2-(3-chloropropyl)-2,3-dihydro-3-hydroxy-4H-1,3-benzoxazin-4-one

HRID 2398044

Reaktionsgleichung

Reaktionsgleichung von HRID 2398044
C(O)(=O)C.Cl.[Cl:6][C:7]1[CH:16]=[C:11]([C:12]([NH:14][OH:15])=[O:13])[C:10]([OH:17])=[CH:9][CH:8]=1.C(O[CH:21](OCC)[CH2:22][CH2:23][CH2:24][Cl:25])C>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:17][CH:21]([CH2:22][CH2:23][CH2:24][Cl:25])[N:14]([OH:15])[C:12](=[O:13])[C:11]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 313Hydrochloric Acid2×HCID 169935Benzamide, 5-chloro-N,2-dihydroxy-HCID 2625984-Chlorobutanal diethyl acetal

Produkt 1

HCID 214345096-Chloro-2-(3-chloropropyl)-2,3-dihydro-3-hydroxy-4H-1,3-benzoxazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-Chloro-2-(3-chloropropyl)-2,3-dihydro-3-hydroxy-4H-1,3-benzoxazin-4-one was prepared by adding 250 ml. of glacial acetic acid saturated with hydrogen chloride gas to 37 g. of 5-chlorosalicylhydroxamic acid. 4-Chlorobutyraldehyde diethyl acetal (34 g.) and 50 ml. of glacial acetic acid saturated with hydrogen chloride gas were then added simultaneously with stirring at a rate to maintain a temperature of 25° to 40° C. The resulting mixture was stirred and heated at 55° to 60° C. for 2 hours and then allowed to stand at room temperature overnight. Mixture was poured into a mixture of ice and water, and when oil solidified it was removed by filtrating, washed with water, and air-dried. The crude product weighed 31.5 g. and melted at 70°-75° C. A sample recrystallized from ligroin at 80°-81° C.

Aufarbeitung

  1. additionby adding 250 ml
  2. temperatureto maintain a temperature of 25° to 40° C
  3. stirringThe resulting mixture was stirred
  4. temperatureheated at 55° to 60° C. for 2 hours
  5. customwas removed
  6. filtrationby filtrating
  7. washwashed with water
  8. customair-dried
  9. customA sample recrystallized from ligroin at 80°-81° C.

Quellen und Nachweise

ORD-Eintrag
ord-8a59f5038dbc4b65ba7b023a5ea2071c
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04024139

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