Thionyl Chloride → HCID 86668998, compound

HRID 2366219Notes

Reaction equation

HRID 2366219 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14])=O.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]([Cl:23])=[N:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 867233092,6-Dichloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-iodobenzamide

Product 1

HCID 86668998HCID 86668998, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6-dichloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-iodobenzamide (2.83 g, 6.4 mmol) in thionyl chloride (23 mL) was heated to 90° C. for 56 hours then diluted with toluene and concentrated under reduced pressure to give the desired compound (2.94 g, 99% yield). 1H NMR (300 MHz, CDCl3): δ 8.22 (d, J=5.1 Hz, 1H), 7.84-7.76 (m, 2H), 6.95 (t, J=5.1 Hz, 1H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53f2f9e8bee840f8a4882030dbcc92b1
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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