Acryloyl chloride → N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chlorophenyl]acrylamide

HRID 630391Notes

Reaction equation

HRID 630391 reaction equation
[Si](OCC1C=CC(N)=C(Cl)C=1)(C(C)(C)C)(C)C.C(Cl)(=O)C=C.C(N(CC)C(C)C)C.[Si:31]([O:38][CH2:39][C:40]1[C:45](OC)=[CH:44][C:43]([NH:48][C:49](=[O:52])[CH:50]=[CH2:51])=[C:42]([Cl:53])[CH:41]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>>[Si:31]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([NH:48][C:49](=[O:52])[CH:50]=[CH2:51])=[C:42]([Cl:53])[CH:41]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 521913N,N-Diethyl-2-propanamineHCID 67145019N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-acrylamideHCID 671452954-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloroaniline2×

Product 1

HCID 67145162N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chlorophenyl]acrylamide

Procedure

Obtained as a white crystalline solid (77%) starting from 4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)-2-chloroaniline (intermediate 46; 2 g; 7.36 mmol), acryloyl chloride (0.78 ml; 9.56 mmol) and diethylisopropylamine (1.92 ml, 11.04 mmol) following the experimental procedure as described for intermediate 40.

Sources & evidence

ORD record
ord-69d900b995554216b9739ce078fcee42
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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