Bromobenzene → 1-Benzyl-3-phenylurea

HRID 1883435

反応式

HRID 1883435 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH:16][C:17]([NH2:19])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CNCCNC>[Cu]I.O1CCOCC1>[CH2:9]([NH:16][C:17]([NH:19][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 7961BromobenzeneHCID 8070N,N'-DimethylethylenediamineHCID 10853BenzylureaHCID 62657Potassium Phosphate, Tribasic

生成物 1

HCID 2803631-Benzyl-3-phenylurea収率 79.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), benzylurea (225 mg, 1.5 mmol, 1.5 equiv), filled with argon. Bromobenzene (105 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylendiamine (22 μL, 0.20 mmol, 0.20 equiv) and dry dioxane (1.0 mL) were added under argon. The test tube was sealed and the reaction mixture was stirred at 80° C. for 25 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with ethyl acetate. The filtrate was concentrated in vacuo. The solid residue was dissolved in ˜2 mL DMF. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 3:1) provided 179 mg (79% yield) of the title compound as a white solid.

後処理

  1. additionfilled with argon
  2. customThe test tube was sealed
  3. temperatureThe resulting suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel
  5. washeluting with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionThe solid residue was dissolved in ˜2 mL DMF
  8. customPurification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 3:1)

出典と根拠

ORDレコード
ord-3bd4478075bd488e8b4de0c1ea3c661b
出典データセット
uspto-grants-2004_07
特許番号
US06759554B2

関連ノート

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