Glycol monoethyl ether → 4-(3-Bromoanilino)-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile

HRID 2213779ノート

反応式

HRID 2213779 の反応式
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=3[S:12][C:3]=12.C(OCCO)C.Cl.N1C=CC=CC=1.[Br:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>>[Br:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH:37][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=3[S:12][C:3]=12

参加物

5

反応物 4

HCID 8076Glycol monoethyl etherHCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 109571994-Chloro-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile

生成物 1

HCID 102242324-(3-Bromoanilino)-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile収率 62%

実験手順

A solution of 400 mg (1.38 mmol) of 4-chloro-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile in 8 mL of 2-ethoxyethanol containing 160 mg (1.38 mmol) of pyridine hydrochloride and 0.180 mL (1.65 mmol) of 3-bromoaniline is heated at reflux for 4 hours. The reaction mixture is filtered hot and the solid is stirred with methanol and ammonium hydroxide. The mixture is poured into water and the solid is collected, washing with ethyl acetate to give 363 mg (62%) of 4-(3-bromoanilino)-8-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile as a brown solid, mp>300° C.

後処理

  1. temperatureat reflux for 4 hours
  2. filtrationThe reaction mixture is filtered hot
  3. additionThe mixture is poured into water
  4. customthe solid is collected
  5. washwashing with ethyl acetate

出典と根拠

ORDレコード
ord-5da32b1757d349fb8bb7685061fbc92e
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

反応ノート

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