Thionyl Chloride → HCID 22736697, compound

HRID 50911Notes

Reaction equation

HRID 50911 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. MW: 367.91; mp:>230° C.; 1H-NMR (CDCl3) δ: 8.98-8.83 (2H, m), 8.25-8.16 (1H, m), 8.10-8.02 (1H, m), 7.76-7.68 (2H, m), 7.60-7.42 (3H, m), 6.78-6.73 (1H, m), 6.61 (1H, d, J=16.1 Hz), 2.75 (3H, s), 2.38 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-86906f5621c84afcbfc6e60d09135be5
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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