Thionyl Chloride → 1-Methyl-4-formylamino-2-pyrrolecarbonyl chloride

HRID 270245Notes

Reaction equation

HRID 270245 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][CH:8]=[O:9])[CH:4]=[C:3]1[C:10]([OH:12])=O.S(Cl)([Cl:15])=O>C1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][CH:8]=[O:9])[CH:4]=[C:3]1[C:10]([Cl:15])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99896091-Methyl-4-formylamino-2-pyrrolecarboxylic acid

Product 1

HCID 118162971-Methyl-4-formylamino-2-pyrrolecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 1-methyl-4-formylamino-2-pyrrolecarboxylic acid (V) in benzene is heated at 80° C. in presence of an excess of thionyl chloride until a solution is obtained. The reaction is then stopped. By repeatedly evaporating from benzene at reduced pressure and temperature, there is obtained the crude chloride (II) which is stocked and used without further purification following determination of the title (generally not below 60%) by conversion to an ester and quantitative analysis of the resulting ester derivative. IR: 1740 cm−1.

Workup

  1. customis obtained
  2. customBy repeatedly evaporating from benzene at reduced pressure and temperature

Sources & evidence

ORD record
ord-8bae6a1098164a79b31eb3d1aa6240bb
Source dataset
uspto-grants-2008_11
Patent number
US07449547B2

Reaction notes

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