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

HRID 649835

Reaction equation

HRID 649835 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a8d27659223a4dc9b26ef01a1b63cb6d
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Linked notes

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