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

HRID 54992ノート

反応式

HRID 54992 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2 回HCID 31297Methanesulfonyl chloride2 回HCID 19957100HCID 19957100、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-663ed390a2f841ae9566f2415b9b0887
出典データセット
uspto-grants-1997_04
特許番号
US05624922

反応ノート

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