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

HRID 989334Notes

Reaction equation

HRID 989334 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e1ae2067dcb34b5590f7469c15bf35c2
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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