Chloroacetyl chloride → HCID 21962569, compound

HRID 2211808Notes

Reaction equation

HRID 2211808 reaction equation
[CH3:1][Si:2]([CH3:26])([C:22]([CH3:25])([CH3:24])[CH3:23])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([OH:11])[CH:10]=1.Cl[CH2:28][C:29](Cl)=[O:30].S(=O)(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>[CH3:26][Si:2]([CH3:1])([C:22]([CH3:23])([CH3:25])[CH3:24])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:29](=[O:30])[CH2:28][O:11][C:9]=2[CH:10]=1

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516919Sodium BisulfateHCID 21045488HCID 21045488, compound

Product 1

HCID 21962569HCID 21962569, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 218852-DimethylaminopyridineSolvent

Procedure

To a stirred solution of 5-(dimethyl-t-butylsilyl)oxymethyl-2-(4-methoxybenzylamino) phenol in anhydrous dichloromethane, triethylamine and dimethylaminopyridine at 0° C. and under nitrogen atmosphere, chloroacetyl-chloride is added. The mixture is refluxed for 10 h, poured into aqueous sodium bisulfate, extracted with dichloromethane and the product isolated by flash chromatography.

Workup

  1. temperatureThe mixture is refluxed for 10 h
  2. extractionextracted with dichloromethane
  3. customthe product isolated by flash chromatography

Sources & evidence

ORD record
ord-b0bf1b623ad640279ae17420df6d2395
Source dataset
uspto-grants-2006_09
Patent number
US07101876B2

Reaction notes

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