3-Bromopentane → 1-Benzyloxy-1-(1-ethylpropyl)-3-phenylurea

HRID 976624

反応式

HRID 976624 の反応式
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].Br[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26]>CN(C)C=O>[CH2:3]([O:10][N:11]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 2542991-(Benzyloxy)-3-phenylureaHCID 178418361HCID 178418361、化合物

生成物 1

HCID 199674391-Benzyloxy-1-(1-ethylpropyl)-3-phenylurea収率 62.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Under a nitrogen atmosphere, a flask was charged with sodium hydride (1.15 g 60% NaH in mineral oil, 29 mmol). Residual oil was washed from the sodium hydride using several portions of hexanes. N,N-Dimethylformamide (50 mL) was added followed by the dropwise addition of a solution of 1-benzyloxy-3-phenylurea (7.0 g, 29 mmol) in N,N-dimethylformamide (20 mL). Hydrogen evolution occurred immediately. The reaction was stirred for 0.5 hr then 3-bromopentane (4.0 mL, 32 mmol) was added dropwise. The reaction mixture was heated at 60° C. for 15 hours then allowed to cool to room temperature. The reaction was quenched with water then extracted with several portions of diethyl ether. The ether extracts were combined, washed with water and brine, dried over magnesium sulfate and then concentrated to provide 8.7 g of crude product as a pale yellow solid. The crude product was purified by flash chromatography (silica gel; 9:1 hexanes:ethyl acetate)to provide 5.7 g of 1-benzyloxy-1-(1-ethylpropyl)-3-phenylurea as a white solid, m.p. 45.0°-45.6° C.

後処理

  1. washResidual oil was washed from the sodium hydride using several portions of hexanes
  2. additionN,N-Dimethylformamide (50 mL) was added
  3. temperatureto cool to room temperature
  4. customThe reaction was quenched with water
  5. extractionthen extracted with several portions of diethyl ether
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto provide 8.7 g of crude product as a pale yellow solid
  10. customThe crude product was purified by flash chromatography (silica gel; 9:1 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-e668a9c0b1f745288d1c305bc250af24
出典データセット
uspto-grants-1997_03
特許番号
US05612377

関連ノート

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