Chloride → N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-methoxyphenyl]acrylamide

HRID 630412Notes

Reaction equation

HRID 630412 reaction equation
[Cl-].C(CC(CC)(NC(C)C)C)C.[Si:13]([O:20][CH2:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])=[C:24](Cl)[CH:23]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>>[Si:13]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])=[CH:26][C:27]=1[O:28][CH3:29])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15]

Participants

4

Reactant 3

HCID 312ChlorideHCID 67145019N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-acrylamideHCID 129867302Diethyldiisopropylamine

Product 1

HCID 67469526N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-methoxyphenyl]acrylamide

Procedure

Obtained as a solid (63%) from [4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-methoxyphenyl]amine (intermediate 99; 5 g, 18.7 mmol), acryloil chloride (1.98 mL, 24.28 mmol) and diethyldiisopropylamine (4.9 mL, 28.06 mmol) following the experimental procedure as described in intermediate 40. The crude obtained was purified by column chromatography with silica gel, eluting with methylene chloride.

Workup

  1. customThe crude obtained
  2. customwas purified by column chromatography with silica gel
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-cdbbf9f8ce6f4afcaeb5d1ad7d278e1e
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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