Bromobenzene → 1-Benzyl-3-phenylurea

HRID 1883435

반응식

HRID 1883435 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 2803631-Benzyl-3-phenylurea수율 79.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3bd4478075bd488e8b4de0c1ea3c661b
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759554B2

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