Dimethylformamide → 4-Cyano-2-methoxybenzoyl chloride

HRID 1005924Notes

Reaction equation

HRID 1005924 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].C(Cl)(=O)C([Cl:17])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:4]=1[C:5]([Cl:17])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 151660044-Cyano-2-methoxybenzoic acid

Product 1

HCID 226750494-Cyano-2-methoxybenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-4-cyanobenzoic acid (Tetrahedron Letters, 1986, 27(49), 5997-6000) (1 g, 5.6 mmol) was dissolved in CH2Cl2 (20 ml). Oxalyl chloride (1.5 ml, 8.2 mmol) was rapidly introduced into the solution and a drop of DMF was added. A vigorous reaction took place with the abundant evolution of gaseous products. The solution was stirred for 1 h then allowed to stand over night. Solvent was removed using a rotary evaporator to leave 1.1 g of an off white solid (5.6 mmol, yield 99%) that was used without further purification.

Workup

  1. customA vigorous reaction
  2. waitto stand over night
  3. customSolvent was removed
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-efa16ed7b03e416fb1e1fb87d1802dd2
Source dataset
uspto-grants-2004_09
Patent number
US06787550B1

Reaction notes

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