Potassium Hydroxide → N-[6-chloro-2-(3-chlorobenzoyl)-1H-indol-3-yl]methanesulfonamide

HRID 651028ノート

反応式

HRID 651028 の反応式
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[N:8](C(OCC)=O)[C:7]=1[C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)(=[O:4])=[O:3].[OH-].[K+]>C(O)C.O>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[C:7]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[NH:8]2)=[CH:13][CH:12]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 21710894Ethyl 3-[bis(methylsulfonyl)amino]-6-chloro-2-(3-chlorobenzoyl)-1H-indole-1-carboxylate

生成物 1

HCID 9821369N-[6-chloro-2-(3-chlorobenzoyl)-1H-indol-3-yl]methanesulfonamide収率 48%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of the ethyl 3-[bis(methylsulfonyl)amino]-6-chloro-2-(3-chlorobenzoyl)-1H-indole-1-carboxylate (step 1, 532 mg, 0.998 mmol) in ethanol (15 ml) was added a solution of potassium hydroxide (395 mg, 5.99 mmol) in water (8 ml) at room temperature. After stirring for 1 h at ambient temperature, the mixture was concentrated to ca. 10 ml, and partioned between with ethyl acetate (150 ml) and water (100 ml). The organic layer was separated and washed with water (100 ml), and dried (Na2SO4). Removal of the solvent by evaporation gave an crystalline residue, which was crystallized from ethanol/hexane to afford 182 mg (48%) of the title compound.

後処理

  1. concentrationthe mixture was concentrated to ca. 10 ml
  2. customThe organic layer was separated
  3. washwashed with water (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent
  6. customby evaporation
  7. customgave an crystalline residue, which
  8. customwas crystallized from ethanol/hexane

出典と根拠

ORDレコード
ord-db66296fe4684e5f99d2e12765540367
出典データセット
uspto-grants-2001_08
特許番号
US06277878B1

反応ノート

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