Ammonium Chloride → 3,5-Dichloro-3-(2,3-dimethoxyphenyl)-1,3-dihydro-2h-indol-2-one

HRID 31347

反応式

HRID 31347 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[O-])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH3:17][O:18][C:19]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=1[C:27](=O)C(OCC)=O.[NH4+].[Cl-:35]>CCOCC.CCCCC.C1COCC1>[Cl:35][C:27]1([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH3:26])[C:19]=2[O:18][CH3:17])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[NH:8][C:9]1=[O:11]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 204558374-ChlorophenylcarbamateHCID 21905960Ethyl 2-(2,3-dimethoxyphenyl)-2-oxoacetateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 219059313,5-Dichloro-3-(2,3-dimethoxyphenyl)-1,3-dihydro-2h-indol-2-one

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

4-chlorophenylcarbamate in 100 ml of ether is cooled to −40° C. under an atmosphere of dry nitrogen, 80 ml of a 1.5 M solution of tert-butyllithium in pentane are added dropwise and the mixture is left stirring at −20° C. for 3 hours. The reaction mixture is cooled to −40° C., a solution of 14 g of the compound obtained in step A in 50 ml of THF is added over 1 hour and the mixture is left stirring for 4 days at RT. The reaction mixture is poured into saturated NH4Cl solution and the precipitate formed is spin-filtered off and dried. 10.2 g of the expected product are obtained and are used without further purification in the following step.

後処理

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled to −40° C.
  3. waitthe mixture is left
  4. stirringstirring for 4 days at RT
  5. customthe precipitate formed
  6. filtrationis spin-filtered off
  7. customdried

出典と根拠

ORDレコード
ord-dd0baaab2fb24258ba4f70e577d6bb6f
出典データセット
uspto-grants-2008_09
特許番号
US07425566B2

関連ノート

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