Methyl 3-carbamoyl-5-iodobenzoate → Methyl 3-cyano-5-iodobenzoate

HRID 2216754Notes

Reaction equation

HRID 2216754 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:14])[CH:13]=1)[C:8]([NH2:10])=O)=[O:4]>S(Cl)(Cl)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[C:7]([C:8]#[N:10])[CH:6]=1

Participants

3

Reactant 1

HCID 21942671Methyl 3-carbamoyl-5-iodobenzoate

Product 1

HCID 21942623Methyl 3-cyano-5-iodobenzoateYield 29%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methoxycarbonyl-5-iodobenzamide (2.5 g, 8.2 mmol) in thionyl chloride (2 mL) was heated for 2 hours at 90° C. The reaction mixture was cooled and concentrated in vacuo. Silica gel chromatography afforded 670 mg (29%) of methyl-3-cyano-5-iodobenzoate, as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4e0955b5d42411daed99a4fb7c6ca84
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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