Sodium Bicarbonate → 4-[4-(4-Fluorophenyl)-2,5-dioxo-4-hydroxymethyl-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389878ノート

反応式

HRID 389878 の反応式
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[CH:9])[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([CH2:10][O:11]CC=C)[C:4](=[O:22])[N:3]1[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:5]2([CH2:10][OH:11])[C:4](=[O:22])[N:3]([C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([C:31]([F:34])([F:32])[F:33])[CH:24]=3)[C:2](=[O:1])[N:6]2[CH2:7][C:8]#[CH:9])=[CH:16][CH:17]=1

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 866414594-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

生成物 1

HCID 593171594-[4-(4-Fluorophenyl)-2,5-dioxo-4-hydroxymethyl-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.45 g of 4-[2,5-dioxo-4-(4-fluorophenyl)-4-[(2-prop enyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile obtained in step 1 is dissolved in 5 mL of DCM under argon atmosphere. 0.2 mL of trifluoroborane-dimethylsulfide complex is added. The mixture is stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution is slowly added. The product is extracted with DCM and the organic layer is dried over sodium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 6/1 DCM/ethyl acetate.

後処理

  1. addition0.2 mL of trifluoroborane-dimethylsulfide complex is added
  2. extractionThe product is extracted with DCM
  3. dry with materialthe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography over silica gel
  7. washwhile eluting with 6/1 DCM/ethyl acetate

出典と根拠

ORDレコード
ord-e893274b670b4daeaccd061e28ed94e1
出典データセット
uspto-grants-2013_02
特許番号
US08383608B2

反応ノート

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