3-Chlorobenzoic Acid → HCID 14901665, compound

HRID 2394829Notes

Reaction equation

[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[CH3:2].ClC1C=C(C=CC=1)C(O)=O.C(NCC)C.[CH3:30][Si:31](Cl)([CH3:33])[CH3:32]>>[Cl:11][C:7]1[C:6]([Si:31]([CH3:33])([CH3:32])[CH3:30])=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([N:3]([CH2:1][CH3:2])[CH2:13][CH3:14])=[O:12]

Participants

Reactant 4

HCID 4473-Chlorobenzoic Acid

HCID 6397Chlorotrimethylsilane

HCID 8021Diethylamine

HCID 6390853-chloro-N,N-diethylbenzamide

Product 1

HCID 14901665HCID 14901665, compoundYield 95%

Procedure

N,N-diethyl-3-chlorobenzamide (10.45 g, 50 mmol) (prepared from 3-chlorobenzoic acid and diethylamine using the procedures described above) was reacted with TMSCl (16.30 g, 150 mmol) using General Method A to afford 13.4 g of the title compound as an orange oil in 95% yield.

Sources & evidence

ORD record: ord-909385bd35194b52ba3df08427a344d6
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811411

Reaction notes

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