Thionyl Chloride → HCID 22736697, compound

HRID 382546Notes

Reaction equation

HRID 382546 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:12])=[CH:5][C:6]=1/[CH:7]=[CH:8]/[C:9](O)=[O:10].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([CH3:12])=[CH:5][C:6]=1/[CH:7]=[CH:8]/[C:9]([Cl:15])=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57125023-(2,5-dimethylthiophen-3-yl)prop-2-enoic Acid

Product 1

HCID 22736697HCID 22736697, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (E)-3-(2,5-dimethylthiophene-3-yl)acrylic acid (328 mg, 1.8 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-3-(2,5-dimethylthiophene-3-yl)acryloyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (250 mg, 1.4 mmol) and (E)-3-(2,5-dimethylthiophene-3-yl)acryloyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate/ethanol yielded the titled compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 60 min
  3. customVolatiles were removed by evaporation

Sources & evidence

ORD record
ord-cbb76a7495614e03a0a5e4790b762903
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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