Boric Acid → 2-(1H-Pyrrol-2-yl)benzo[d]thiazole

HRID 6430

反応式

HRID 6430 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](O)=O.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].B(O)(O)O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

参加物

6

反応物 3

HCID 7628Boric AcidHCID 87132-AminothiophenolHCID 12473Pyrrole-2-Carboxylic Acid

生成物 1

HCID 1356254832-(1H-Pyrrol-2-yl)benzo[d]thiazole収率 14%

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5.55 g (50 mmol) of pyrrole-2-carboxylic acid, 6.26 g (50 mmol) of 2-aminothiophenol and 3.09 g (50 mmol) of boric acid in 250 mL of xylene was heated under reflux for 3 days while removing water which was generated from reaction using a Dean-Stark trap. the cooled reaction mixture was diluted with 200 mL of ethyl acetate, washed with 200 mL of 5% sodium hydroxide solution and then with 200 mL of water. The separated organic layer was dried over anhydrous sodium sulfate. The resulting crude product was purified by column chromatography on silica gel with 10% ethyl acetate in hexane as eluant. The desired product, 2-(pyrrol-2-yl)benzothiazole (1.40 g, 14%) was obtained as a pale yellow solid. m.p. 150°-151° C.; 1H-NMR (CDCl3) 6.32-6.35 (m, 1H, ArH), 6.87-6.89 (m, 1H, ArH), 6.94-6.96 (m, 1H, ArH), 6.33 (t, 1H, ArH), 6.43 (t, 1H, ArH), 7.84 (d, 1H, ArH), 7.90 (d, 1H, ArH).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. customwhile removing water which
  4. customwas generated from reaction
  5. customthe cooled reaction mixture
  6. washwashed with 200 mL of 5% sodium hydroxide solution
  7. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  8. customThe resulting crude product was purified by column chromatography on silica gel with 10% ethyl acetate in hexane as eluant

出典と根拠

ORDレコード
ord-514be903fc7a4ed1b961eb5abfbc5505
出典データセット
uspto-grants-1993_09
特許番号
US05248782

関連ノート

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