Sodium Chloride → methyl N-[3-(3,4-dichlorophenyl)benzyl]carbamate

HRID 1168028ノート

反応式

HRID 1168028 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][NH:6][C:7](=[O:10])[O:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:22]=[C:23](OB(O)O)[CH:24]=[CH:25][C:26]=1[Cl:27].[Cl-].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[CH2:5][NH:6][C:7](=[O:10])[O:8][CH3:9])[CH:24]=[CH:25][C:26]=1[Cl:27]

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 12090302Methyl (3-bromobenzyl)carbamateHCID 219399273,4-Dichloro-phenyl-boric acid

生成物 1

HCID 12090301methyl N-[3-(3,4-dichlorophenyl)benzyl]carbamate収率 94.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

1.30 g of methyl N-(3-bromobenzyl)carbamate, 0.56 g of sodium carbonate in aqueous solution (20 ml) and 0.13 g of tetrakis(triphenylphosphine)palladium (0) were added to toluene (40 ml) under a nitrogen atmosphere. The resulting solution was mixed with 1.02 g of 3,4-dichlorophenylboric acid in ethanol (20 ml) at room temperature with stirring and refluxed under heating for 2 hours. After the reaction, the reaction solution was cooled to room temperature, poured into saturated aqueous sodium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 1.45 g of methyl N-[3-(3,4-dichlorophenyl)benzyl]carbamate as a yellow transparent viscous liquid.

後処理

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure for removal of the solvent
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3e5923a69dfd4da18e8f75f5ae234dfe
出典データセット
uspto-grants-2003_09
特許番号
US06620961B1

反応ノート

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