Thionyl Chloride → 3,4-Dichloro-5-cyano-1H-pyrrole-2-carbonyl chloride

HRID 2233897Notes

Reaction equation

HRID 2233897 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]#[N:9])[NH:4][C:3]=1[C:10]([OH:12])=O.S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]#[N:9])[NH:4][C:3]=1[C:10]([Cl:15])=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 251376833,4-Dichloro-5-cyano-1H-pyrrole-2-carboxylic acid2×

Product 1

HCID 860383333,4-Dichloro-5-cyano-1H-pyrrole-2-carbonyl chloride

Procedure

3,4-Dichloro-5-cyano-1H-pyrrole-2-carboxylic acid (Intermediate 131, 0.9 g, 0.2 mmol) was dissolved in excess thionyl chloride (5 ml) and heated to reflux for 30 minutes. The reaction mixture was concentrated and the residue was dissolved in THF and concentrated (×2). The solid (0.82 g, 89%) was pumped to dryness and stored under argon.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in THF
  5. concentrationconcentrated (×2)

Sources & evidence

ORD record
ord-e58e1c29b64a4b82be79289751a23322
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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