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

HRID 1769147Notes

Reaction equation

HRID 1769147 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-837d3321780f4bad92b464e1c6285943
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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