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Hydrochloric Acid → 1-(5-Bromo-7-pyridin-2-yl-benzothiazol-2-yl)-3-ethyl-urea

HRID 1010674
ノート
印刷プレビュー

反応式

HRID 1010674 の反応式
[Br:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.[Br-].[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Zn+].Cl>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.O>[Br:1][C:2]1[CH:3]=[C:4]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=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

6

反応物 3

HCID 313Hydrochloric AcidHCID 578135675,7-Dibromo-benzothiazol-2-yl-3-ethyl ureaHCID 178418723HCID 178418723、化合物

生成物 1

HCID 578136111-(5-Bromo-7-pyridin-2-yl-benzothiazol-2-yl)-3-ethyl-urea収率 55.2%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒
HCID 962
Water
溶媒

反応条件

温度
55 °C

実験手順

A stirred mixture of the 1-(5,7-dibromo-benzothiazol-2-yl-3-ethyl urea (2.62 g, 0.00687 mol) and Dichlorobis(triphenylphosphine)-palladium (0.48 g 0.000687 mol), under nitrogen, was treated in one portion, via a syringe, with 2-pyridyl zinc bromide solution (0.5M solution in THF, 7.66 g, 0.0344 mol). The reaction mixture was heated, with stirring, at 55° C. for 18 hours, allowed to cool and poured into 500 ml of water containing ˜5 ml of conc hydrochloric acid. The suspension was stirred and the solid filtered off, washed with water, followed by 20 ml of 1:1 DCM/Methanol mixture to give the crude 1-(5-Bromo-7-pyridin-2-yl-benzothiazol-2-yl)-3-ethyl-urea (1.43 g). This was purified by “flash” silica chromatography using 0 to 100% hexane/ethyl acetate followed by 0 to 100% methanol in ethyl acetate to elute the required product as a beige solid (1.1 g).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto cool
  3. stirringThe suspension was stirred
  4. filtrationthe solid filtered off
  5. washwashed with water

出典と根拠

ORDレコード
ord-a6ef806caed44a14894e7daf2f38b3b1
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977340B2

反応ノート

読み込み中…

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