Thionyl Chloride → HCID 23049338, compound

HRID 2106858Notes

Reaction equation

HRID 2106858 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]([Cl:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23049308HCID 23049308, compound

Product 1

HCID 23049338HCID 23049338, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7-Phenylhept-2E-en-6-ynoic acid (2 g) was dissolved in benzene (20 ml), thionyl chloride (2.5 ml) was added, and the mixture was refluxed under a nitrogen atmosphere for 45 minutes. Benzene and excess thionyl chloride were removed under reduced pressure and the residue was treated with benzene (2×4 ml), followed by evaporation, to leave a residue of 7-phenylhept-2E-en-6-ynoyl chloride. The acid chloride was dissolved in ether (20 ml), and triethylamine (1.5 ml) and isobutylamine (3 ml) were added. The mixture was stirred at room temperature for 2 hours then cooled to 0° C. The mixture was filtered and the filtrate was subjected to chromatography on silica (60 g), eluting with 100% hexane grading to 100% ether, to yield N-isobutyl-7-phenylhept-2E-en-6-ynamide mp 86°-8° C.

Workup

  1. temperaturethe mixture was refluxed under a nitrogen atmosphere for 45 minutes
  2. customBenzene and excess thionyl chloride were removed under reduced pressure
  3. additionthe residue was treated with benzene (2×4 ml)
  4. customfollowed by evaporation

Sources & evidence

ORD record
ord-55ac91ce31214e8eb2d9a2417b28707a
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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