Hydrochloric Acid → 2-methyl-4-(4-methylsulfonylaminophenyl)-1-(2H)-phthalazinone

HRID 54992Notes

Reaction equation

HRID 54992 reaction equation
[CH3:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>C(Cl)Cl>[CH3:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 19957100HCID 19957100, compound

Product 1

HCID 199571022-methyl-4-(4-methylsulfonylaminophenyl)-1-(2H)-phthalazinoneYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-methyl-4-(4-aminophenyl)-1-(2H)-phthalazinone (8.77 g, 34.9 mmol), CH2Cl2 (300 mL) and pyridine (3.11 mL, 38.4 mmol) at 0° C. was added dropwise methanesulfonyl chloride (2.97 mL, 38.4 mmol) in CH2Cl2 (20 mL) over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 12 hours. Additional pyridine (0.5 mL) and methanesulfonyl chloride (0.5 mL) was added and the mixture was stirred as such for 2 hours. The reaction mixture was poured into 2N HCl, the organic layer was separated and then washed with water and dried over Na2SO4. The solvent was removed in vacuo and the residue was azeotroped with toluene and CH2Cl2 to afford 9.0 g (78%) of 2-methyl-4-(4-methylsulfonylaminophenyl)-1-(2H)-phthalazinone as a yellow solid.

Workup

  1. stirringthe mixture was stirred as such for 2 hours
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was azeotroped with toluene and CH2Cl2

Sources & evidence

ORD record
ord-663ed390a2f841ae9566f2415b9b0887
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

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