Potassium Carbonate → 6-(2-Picolinyloxy)-2-cyanobenzothiazole

HRID 424454ノート

反応式

HRID 424454 の反応式
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[C:10]([C:12]1[S:13][C:14]2[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=2[N:16]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:21][C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([C:10]#[N:11])[S:13][C:14]=2[CH:20]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 98819122-Cyano-6-hydroxybenzothiazole

生成物 1

HCID 584277576-(2-Picolinyloxy)-2-cyanobenzothiazole収率 72%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

(Bromomethyl)pyridine hydrobromide (1.87 g, 7.38 mmol) and 2-cyano-6-hydroxybenzothiazole (1.00 g, 5.68 mmol) were suspended in acetone (50 mL). After introduction of potassium carbonate (1.96 g, 14.2 mmol), the suspension was refluxed for 72 h under nitrogen. After cooling down the mixture and filtering the solids, the filtrate was concentrated and the residue was purified by silica gel chromatography using 50%-75% ethyl acetate in heptane. A yellowish solid was obtained in 72% yield. MS (ESI+): m/z 267.90 (M+H)+; calc'd: 268.05.

後処理

  1. temperatureAfter cooling down the mixture
  2. filtrationfiltering the solids
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. customA yellowish solid was obtained in 72% yield

出典と根拠

ORDレコード
ord-037cc8f24fc549f3a6c5c9059834df06
出典データセット
uspto-grants-2012_01
特許番号
US08106052B2

反応ノート

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