Pyridine → 2-(Acetyloxy)-5-(aminosulfonyl)benzoic acid hemihydrate

HRID 981063ノート

反応式

HRID 981063 の反応式
[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([OH:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22].[Cl-].[Na+]>C(#N)C.C(OCC)(=O)C>[OH2:3].[C:21]([O:14][C:8]1[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])(=[O:23])[CH3:22].[C:21]([O:14][C:8]1[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])(=[O:23])[CH3:22]

参加物

7

反応物 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 77312702-Hydroxy-5-sulfamoylbenzoic acid

生成物 1

HCID 679299742-(Acetyloxy)-5-(aminosulfonyl)benzoic acid hemihydrate収率 65.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-(Aminosulfonyl)-2-hydroxybenzoic acid (9.35 g, 0.043 mole) was suspended in 50 ml acetonitrile. Pyridine (4.04 ml, 0.05 mole) was added with stirring. The resulting solution was chilled in an ice bath. Acetylchloride (3.63 ml, 0.05 mole) was added dropwise in two minutes and the reaction mixture was stirred at room temperature for four hours. To the reaction mixture was added about 50 ml each of ethyl acetate and sodium chloride solution. The organic layer was separated and extracted once more with sodium chloride solution. The aqueous layers were back extracted with acetonitrile-ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to a white solid. The solid was triturated in ethyl acetate and isopropyl ether with small amount of acetonitrile overnight. The solid was collected, rinsed and dried under vacuum pump pressure to give 5.03 g of title compound, mp 179°-181° C.

後処理

  1. temperatureThe resulting solution was chilled in an ice bath
  2. stirringthe reaction mixture was stirred at room temperature for four hours
  3. customThe organic layer was separated
  4. extractionextracted once more with sodium chloride solution
  5. extractionThe aqueous layers were back extracted with acetonitrile-ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid
  9. customThe solid was triturated in ethyl acetate
  10. customwith small amount of acetonitrile overnight
  11. customThe solid was collected
  12. washrinsed
  13. customdried under vacuum pump pressure

出典と根拠

ORDレコード
ord-5c9b4c23cfbf4e0fa25e8d8b493dddfd
出典データセット
uspto-grants-1991_02
特許番号
US04990523

反応ノート

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