Hydrochloric Acid → 4-Chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid

HRID 1580828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1580828
[Cl:1][C:2]1[C:10]([S:11](Cl)(=[O:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].N[CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].C[N:30](C)C=O.Cl>O>[Cl:1][C:2]1[C:10]([S:11](=[O:13])(=[O:12])[NH:30][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22][C:20](=[O:21])[CH3:19])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acidHCID 2083842-Aminoacetanilide

Produkt 1

HCID 215589374-Chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The starting material is prepared as follows: The mixture of 38.8 g 4-chloro-5-chlorosulfonyl-3-nitrobenzoic acid, 39.9 g of 2-aminoacetanilide and 150 ml of dimethylformamide is stirred for 21/2 hours at room temperature. It is poured into 1.7 lt of water and 20 ml of concentrated hydrochloric acid while stirring, the precipitate formed is filtered off and washed with water. It is dissolved in 600 ml of hot ethanol, 900 ml of hot water are added, the mixture filtered and the filtrate left in the cold, to yield the 4-chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid melting at 225°-227° with decomposition. [In the analogous manner the 5-(4-acetamidophenylsulfamoyl)-isomer is prepared, m.p. 245°-246° (dec.).]

Aufarbeitung

  1. customThe starting material is prepared
  2. stirringwhile stirring
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. dissolutionIt is dissolved in 600 ml of hot ethanol
  7. addition900 ml of hot water are added
  8. filtrationthe mixture filtered
  9. waitthe filtrate left in the cold,

Quellen und Nachweise

ORD-Eintrag
ord-0ccf42553e5c4925ab0020e4e6555b4a
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03933906

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