Water → 5-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethyl-N-methylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

HRID 234509ノート

反応式

HRID 234509 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6](=[O:28])[C:5]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[N:29]([CH3:31])[CH3:30].[H-].[Na+].[CH3:41]I.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([N:20]([CH3:41])[C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22])=[CH:18][CH:19]=1)(=[O:13])=[O:12])[C:6](=[O:28])[C:5]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[N:29]([CH3:30])[CH3:31]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 190765585-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

生成物 1

HCID 190766165-Chloro-3-(2-chlorophenyl)-1-[4-(N',N'-diethyl-N-methylureido)benzenesulfonyl]-1,3-dihydro-3-(dimethylamino)indol-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 0.420 g of the compound obtained in EXAMPLE 30 in 7 ml of DMF is cooled to 0° C. under an argon atmosphere and 0.027 g of sodium hydride as an 80% dispersion in oil is added. After stirring for 30 minutes, 0.05 ml of methyl iodide is added and the reaction mixture is stirred for 10 minutes. It is poured into water, extracted with AcOEt, washed with water, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=0.211 g. M.p.=145°-148° C.

後処理

  1. stirringthe reaction mixture is stirred for 10 minutes
  2. extractionextracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum
  6. customThe residue is chromatographed on silica

出典と根拠

ORDレコード
ord-05a518efea4142d7aba13c86e02171f7
出典データセット
uspto-grants-1997_01
特許番号
US05594023

反応ノート

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