Sulfuric Acid → 4[2{2(4-Sulfophenyl)ethylsulfonyl}4-nitrophenylazo]5-morpholinosulfonamido-1-naphthol

HRID 1390088

Reaktionsgleichung

Reaktionsgleichung von HRID 1390088
S(=O)(=O)(O)O.[N:6]([O-])=O.[Na+].[S:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][S:22]([C:25]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:26]=2[NH2:27])(=[O:24])=[O:23])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11].[O:35]1[CH2:40][CH2:39][N:38]([S:41]([NH:44][C:45]2[CH:54]=[CH:53][CH:52]=[C:51]3[C:46]=2[CH:47]=[CH:48][CH:49]=[C:50]3[OH:55])(=[O:43])=[O:42])[CH2:37][CH2:36]1.C([O-])(=O)C.[Na+]>O.C(O)C.C(O)(=O)C>[S:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][S:22]([C:25]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:26]=2[N:27]=[N:6][C:47]2[C:46]3[C:51](=[CH:52][CH:53]=[CH:54][C:45]=3[NH:44][S:41]([N:38]3[CH2:39][CH2:40][O:35][CH2:36][CH2:37]3)(=[O:43])=[O:42])[C:50]([OH:55])=[CH:49][CH:48]=2)(=[O:23])=[O:24])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11]

Komponenten

9

Edukt 5

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 202948662[2(4-Sulfophenyl)ethylsulfonyl]-4-nitroanilineHCID 202948755-Morpholinosulfonamido-1-naphtholHCID 23668193Sodium Nitrite

Produkt 1

HCID 1361093794[2{2(4-Sulfophenyl)ethylsulfonyl}4-nitrophenylazo]5-morpholinosulfonamido-1-naphthol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To 3 ml. of conc. sulfuric acid under cooling was added 0.43 g. of sodium nitrite, dissolved by heating and, after cooling, 5.5 ml. of acetic acid were added thereto. The resulting solution was cooled to 5° C. and 2.32 g. of 2[2(4-sulfophenyl)ethylsulfonyl]-4-nitroaniline were added thereto with stirring. Stirring was continued at room temperature for 3 hours to prepare a diazonium salt solution. Separately, a solution of 1.85 g. of 5-morpholinosulfonamido-1-naphthol in 250 ml. of ethanol and 30 ml. of water was prepared, and a solution of 15 g. of sodium acetate in 40 ml. of water was added thereto with stirring. To the resulting solution, the diazonium salt solution as prepared above was added dropwise under ice-cooling. The reaction mixture was stirred at about 50° C. for 2 hours. Thereafter, the mixture was concentrated to about 100 ml., the precipitate thus separated was recovered by filtration and dried to give 4.3 g. of the desired product.

Aufarbeitung

  1. additionwas added 0.43 g
  2. temperatureby heating
  3. temperatureafter cooling
  4. stirringStirring
  5. stirringwith stirring
  6. additionabove was added dropwise under ice-
  7. temperaturecooling
  8. stirringThe reaction mixture was stirred at about 50° C. for 2 hours
  9. concentrationThereafter, the mixture was concentrated to about 100 ml
  10. custom, the precipitate thus separated
  11. filtrationwas recovered by filtration
  12. customdried
  13. customto give 4.3 g

Quellen und Nachweise

ORD-Eintrag
ord-4b9cac2f78474071ac80be99cc349107
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04247629

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