Diisopropylethylamine → (3-Chloro-4-vinyl-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

HRID 1249844

반응식

HRID 1249844 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[CH:8]=[CH2:9].C(N(C(C)C)CC)(C)C.[CH3:20][Si:21]([CH3:38])([CH3:37])[CH2:22][CH2:23][O:24][C:25](ON1C2C=CC=CC=2N=N1)=[O:26]>CN(C)C=O.O>[CH3:20][Si:21]([CH3:38])([CH3:37])[CH2:22][CH2:23][O:24][C:25](=[O:26])[NH:10][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH2:9])=[C:2]([Cl:1])[CH:3]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 138923191-(((2-(Trimethylsilyl)ethoxy)carbonyl)oxy)-1H-benzotriazoleHCID 185430893-Chloro-4-vinyl-phenylamine

생성물 1

HCID 18543726(3-Chloro-4-vinyl-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-chloro-4-vinyl-phenylamine (3.4 g) in N,N-dimethylformamide (44 mL) containing diisopropylethylamine (5.8 mL) is added 1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (7.1 g) and the mixture is stirred at room temperature under an atmosphere of argon for three days. The solution is then diluted with water and extracted three times with diethyl ether. The combined organic extracts are washed successively with water, saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue is chromatographed over silica gel (10% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a yellow oil.

후처리

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic extracts are washed successively with water, saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is chromatographed over silica gel (10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-7e718f9461cc4b8ba82c8301294df6c4
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06335350B1

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