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Benzene → 4-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)sulfamoyl]benzoic acid

HRID 1517493
ノート
印刷プレビュー

反応式

HRID 1517493 の反応式
[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH2:14].C1C=CC=CC=1.Cl[S:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)(=[O:24])=[O:23].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH:14][S:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:32][CH:33]=1)(=[O:24])=[O:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 823854-(Chlorosulfonyl)benzoic acidHCID 584205805,6,6a,7,8,9-hexahydro-4H-2-phenalenylamine

生成物 1

HCID 673911474-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)sulfamoyl]benzoic acid収率 75.2%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 1049Pyridine溶媒

実験手順

5,6,6a,7,8,9-Hexahydro-4H-2-phenalenylamine (0.130 g) was dissolved in pyridine (5 ml) and anhydrous benzene (2 ml), the solution was added with 4-chlorosulfonylbenzoic acid (0.161 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight at room temperature. The reaction mixture was made to be at 60° C., stirred for 3 hours, left to cool, then added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethyl acetate-n-hexane to obtain the title compound (0.194 g, yield: 75%) as brown needles (melting point: 266-268° C.).

後処理

  1. customto be at 60° C.
  2. stirringstirred for 3 hours
  3. waitleft
  4. temperatureto cool
  5. extractionmade acidic, and the mixture was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-e47344bdb40146ae8c4c978453ba329e
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08232300B2

反応ノート

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