Hydrochloric Acid → 5-Amino-1-(4-chlorophenyl)-4-(4-sulfophenylazo)pyrazole

HRID 459673

Reaktionsgleichung

Reaktionsgleichung von HRID 459673
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].C([O-])(=O)C.[Na+].[NH2:17][C:18]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:21]=[CH:20][CH:19]=1.C([N:32](CC)CC)C.Cl>O>[NH2:17][C:18]1[N:22]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[N:21]=[CH:20][C:19]=1[N:32]=[N:9][C:6]1[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8479Sulfanilic acidHCID 517045Sodium AcetateHCID 122043801-(4-Chlorophenyl)-1H-pyrazol-5-amine

Produkt 1

HCID 1357726935-Amino-1-(4-chlorophenyl)-4-(4-sulfophenylazo)pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

20.8 g (0.12 mol) of sulfanilic acid was diazotized and to the mixture was then added with continuing ice cooling 18.9 g (0.23 mol) of sodium acetate. The dimethylformamide solution from Step 10.1 was added dropwise over a period of 30 minutes. During the addition, the suspension changed color from gray to yellow-brown. The mixture was allowed to agitate an additional 2 h at 5° C. after which it was allowed to stand overnight at room temperature. The next day, the reaction product was filtered off, the moist filter cake was suspended in 350 mL of dimethylformamide and heated to about 80° C. Then, first 19.2 g (0.19 mol) of triethylamine and then 100 mL of water were added to dissolve the intermediate product. The clear solution was allowed to agitate in the presence of 3.5 g of activated carbon for about 15 minutes and was then filtered warm. The residue on the filter was washed with a small amount of water. To the still warm filtrate was then added 17.8 mL (0.21 mol) of concentrated hydrochloric acid, and the resulting yellow suspension was cooled to 0 to 5° C. The precipitated product was removed by suction filtration and washed with 15-mL portions of isopropanol. The residue was dried at 60° C. This gave 23.8 g (63% of the theoretical) of 5-amino-1-(4-chlorophenyl)-4-(4-sulfophenylazo)pyrazole. Melting point; 260° C. (decomp.).

Aufarbeitung

  1. additionDuring the addition
  2. waitto stand overnight at room temperature
  3. filtrationThe next day, the reaction product was filtered off
  4. temperatureheated to about 80° C
  5. dissolutionto dissolve the intermediate product
  6. stirringto agitate in the presence of 3.5 g of activated carbon for about 15 minutes
  7. filtrationwas then filtered
  8. temperaturewarm
  9. washThe residue on the filter was washed with a small amount of water
  10. temperaturethe resulting yellow suspension was cooled to 0 to 5° C
  11. customThe precipitated product was removed by suction filtration
  12. washwashed with 15-mL portions of isopropanol
  13. customThe residue was dried at 60° C

Quellen und Nachweise

ORD-Eintrag
ord-c22908b343d7481b96814bac56d6d652
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07195649B2

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