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

HRID 2187133Notes

Reaction equation

HRID 2187133 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-8aafd9502b4e4a5eafac1fc0cc0c67d2
Source dataset
uspto-grants-2002_06
Patent number
US06407249B1

Reaction notes

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