Phenylacetylene → HCID 14405340, compound

HRID 2232388Notes

Reaction equation

HRID 2232388 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:10]1[S:14][C:13]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[N:12][CH:11]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[C:1]1([C:7]#[C:8][C:10]2[S:14][C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[N:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 21283714HCID 21283714, compound

Product 1

HCID 14405340HCID 14405340, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

In a manner similar to Step D of Example 1, the reaction of 1.3 gram (0.013 mole) of phenylacetylene, 50 ml of triethylamine, 3.2 grams (0.011 mole) of 5-iodo-2-(thien-2-yl)thiazole, 0.080 gram (1.1×10-4 mole) of dichlorobis(triphenylphosphine)palladium (II), and 0.022 gram (1.1×10-4 mole) of copper(I) iodide produced 2.1 grams of 1-phenyl-2-[2-(thien-2-yl)thiazol-5-yl]ethyne as a solid, m.p. 94°-96° C., Compound 22 of Table 1.

Sources & evidence

ORD record
ord-ad8dc8c5acc44af69892a32e55ce8e67
Source dataset
uspto-grants-1988_11
Patent number
US04788207

Reaction notes

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