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Phenylacetylene → 2-(4-Phenylethynylphenyl)benzthiazole

HRID 329767
ノート
印刷プレビュー

反応式

HRID 329767 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10821PhenylacetyleneHCID 23206022-(4-Bromophenyl)benzothiazole

生成物 1

HCID 147663562-(4-Phenylethynylphenyl)benzthiazole収率 79.2%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 8471Triethylamine溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5a32448d536849459431408c03ef5e73
出典データセット
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04892953

反応ノート

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