Dichloromethane → HCID 59574442, compound

HRID 2092052Notes

Reaction equation

HRID 2092052 reaction equation
ClCCl.[CH3:4][O:5][N:6]([CH3:14])[C:7]([C:9]1[CH:10]=[N:11][NH:12][CH:13]=1)=[O:8].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH3:4][O:5][N:6]([CH3:14])[C:7]([C:9]1[CH:13]=[N:12][N:11]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 59574435HCID 59574435, compound

Product 1

HCID 59574442HCID 59574442, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A dichloromethane solution (3 mL) of N-methoxy-N-methyl-1H-pyrazole-4-carboxamide (142.7 mg, 2.68 mmol) was mixed with 2-(trimethysilyl)ethoxymethyl chloride (0.47 mL, 2.68 mmol) and N,N-diisopropylethylamine (0.94 mL, 5.36 mmol) and stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was mixed with ethyl acetate washed with saturated aqueous sodium chloride and the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to give the desired product (325.8 mg, 85% yield).

Workup

  1. customAfter completion of the reaction
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c843254005ae46e39f0824f04dcafdb6
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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