Dimethylformamide → HCID 86608726, compound

HRID 2374733Notes

Reaction equation

HRID 2374733 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].CN(C=O)C.C(Cl)(=O)C([Cl:23])=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([Cl:23])=[O:14])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 691581763-Cyano-4-fluorobenzenepropanoic acid

Product 1

HCID 86608726HCID 86608726, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-Cyano-4-fluorophenyl)-propionic acid (Int. A7) was dissolved in dichloromethane (30 ml) containing 0.1 ml DMF and oxalyl chloride (0.79 g, 6.2 mmol) added dropwise over 5 min. The reaction mixture was stirred for 2 h then concentrated in vacuo to yield the title compound as an oil (1.3 g, 100%). 1H-NMR (CDCl3) δ 3.02 (2H, t), 3.21 (2H, t), 7.13 (1H, t), 7.45 (2H, m).

Workup

  1. additionadded dropwise over 5 min
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-dc95666d271a4e529e11b0d5c32e7f1b
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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