Hydrochloric Acid → 2-methyl-4-(3-methylsulfonylamino-4-chlorophenyl)-1-(2H)-phthalazinone

HRID 1769147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769147
[CH3:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([NH2:19])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20].[CH3:21][S:22](Cl)(=[O:24])=[O:23].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([NH:19][S:22]([CH3:21])(=[O:24])=[O:23])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 199571472-methyl-4-(3-amino-4-chlorophenyl)-1-(2H)-phthalazinone

Produkt 1

HCID 199571582-methyl-4-(3-methylsulfonylamino-4-chlorophenyl)-1-(2H)-phthalazinoneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 2-methyl-4-(3-amino-4-chlorophenyl)-1-(2H)-phthalazinone (38.72 g, 0,136 mol), CH2Cl2 (380 mL) and pyridine (75 mL) at 0° C. was added methanesulfonyl chloride (15.75 mL) in CH2Cl2 (75 mL). The reaction mixture was stirred overnight, poured into 1N HCl (400 mL) and stirred for 45 minutes. The mixture was filtered and the filtrate layers were separated. The solid thus obtained was treated with saturated NaHCO3, filtered, stirred with hexane, then filtered, stirred with hot methanol, then filtered and finally stirred with hot ethyl acetate and filtered to afford 38.8 g (78%) of 2-methyl-4-(3-methylsulfonylamino-4-chlorophenyl)-1-(2H)-phthalazinone, m.p. 234°-236° C.

Aufarbeitung

  1. stirringstirred for 45 minutes
  2. filtrationThe mixture was filtered
  3. customthe filtrate layers were separated
  4. customThe solid thus obtained
  5. filtrationfiltered
  6. stirringstirred with hexane
  7. filtrationfiltered
  8. stirringstirred with hot methanol
  9. filtrationfiltered
  10. stirringfinally stirred with hot ethyl acetate
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-837d3321780f4bad92b464e1c6285943
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380721

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