Hydrochloric Acid → HCID 86746384, compound

HRID 374280Notes

Reaction equation

HRID 374280 reaction equation
[C:1]([S:9]/[CH:10]=[CH:11]\[C:12](Cl)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([NH2:18])[C:16]#[CH:17].C(N(CC)CC)C.Cl>ClCCl>[CH2:15]([NH:18][C:12](=[O:13])/[CH:11]=[CH:10]\[S:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:16]#[CH:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 239041PropargylamineHCID 86746383HCID 86746383, compound

Product 1

HCID 86746384HCID 86746384, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of 0.70 g (0.0039 mol) of cis-3-(benzoylthio)propenoyl chloride in 40 ml of dichloromethane under nitrogen was added dropwise 0.21 ml (0.0039 mol) of propargylamine as a solution in 10 ml of dichloromethane. After 15 min, 0.43 ml (0.0039 mol) of triethylamine was added dropwise. The reaction was allowed to stir at 0° C. for 2 h, poured into 10% aqueous hydrochloric acid, and extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, and dried over magnesium sulfate. Filtration and removal of solvents gave 0.49 g (65% yield) of N-(2-propynyl)-cis-3-(benzoylthio)acrylamide as a white powder, m.p. 131°-134° C., as described in Table 1.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and removal of solvents

Sources & evidence

ORD record
ord-18f9be7164d24c41a4ffd9a40b85e934
Source dataset
uspto-grants-1992_11
Patent number
US05166390

Reaction notes

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