Phenylacetylene → 2-(4-Phenylethynylphenyl)benzthiazole

HRID 329767Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:17]1([C:23]#[C:24][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[S:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution containing 2-(4-bromophenyl)benzthiazole (43.5 g 0.15 mol) and phenylacetylene (20 g, 0.19 mol) in 0.8 L of triethylamine was added the catalyst system consisting of dichlorobis-(triphenylphosphine)palladiumII (1 g), triphenylphosphine (0.3 g) and cuprous iodide (0.1 g). The reaction mixture was refluxed under a nitrogen atmosphere for 19 h. After cooling to 25° C., the reaction mixture was filtered and the filtrate poured into 3 L of water. The resulting light gray solid was isolated by filtration and dried in an oven at 110° C. Recrystallization from heptane using activated charcoal gave 37 g (78.9%) of a white crystalline product: m.p. 172°-173° C.

Workup

additionwas added the catalyst system
temperatureThe reaction mixture was refluxed under a nitrogen atmosphere for 19 h
filtrationthe reaction mixture was filtered
additionthe filtrate poured into 3 L of water
customThe resulting light gray solid was isolated by filtration
customdried in an oven at 110° C
customRecrystallization from heptane using activated charcoal

Sources & evidence

ORD record: ord-5a32448d536849459431408c03ef5e73
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04892953

Reaction notes

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