Triethylamine → HCID 86746382, compound

HRID 374278Notes

Reaction equation

HRID 374278 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].C(N(CC)CC)C.[C:13]([OH:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:13]([S:20]/[CH:3]=[CH:2]\[C:1]([OH:5])=[O:4])(=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10110Propiolic AcidHCID 178526132HCID 178526132, compound

Product 1

HCID 86746382HCID 86746382, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of 15.4 ml (0.25 mol) of propiolic acid in 200 ml of absolute ethanol under nitrogen was added 3.48 ml (0.025 mol) of triethylamine. After 5 min, 33 ml (0.28 mol) of thiobenzoic acid was added very cautiously and dropwise. The exothermic reaction led to the ethanol reaching reflux despite the ice-water bath. After 15 min a solid precipitated from the orange solution. After 2 h at 0° C. the reaction mixture was filtered and the solid was washed twice with absolute ethanol and twice with chloroform to afford 18.3 g (35% yield of cis-3-(benzoylthio)propenoic acid as a white powder.

Workup

  1. customThe exothermic reaction
  2. customAfter 15 min a solid precipitated from the orange solution
  3. filtrationAfter 2 h at 0° C. the reaction mixture was filtered
  4. washthe solid was washed twice with absolute ethanol and twice with chloroform

Sources & evidence

ORD record
ord-f3f45468458f416285c1aa50a55849c5
Source dataset
uspto-grants-1992_11
Patent number
US05166390

Reaction notes

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