Sodium hydride → 6-Fluoro-2-(2-nitroanilino)benzo[b]thiophene-3-carbonitrile

HRID 649943Notes

Reaction equation

HRID 649943 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:12]#[N:13].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[H-].[Na+]>O1CCCC1>[F:11][C:8]1[CH:9]=[CH:10][C:4]2[C:3]([C:12]#[N:13])=[C:2]([NH:1][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])[S:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 184221842-Amino-6-fluorobenzo[b]thiophene-3-carbonitrile

Product 1

HCID 184221416-Fluoro-2-(2-nitroanilino)benzo[b]thiophene-3-carbonitrileYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-fluorobenzo[b]thiophene-3-carbonitrile (15 g), tetrahydrofuran (140 ml) and 2-fluoronitrobenzene (11.3 g) was added portionwise 60% sodium hydride (3.5 g) under ice-cooling and the mixture was stood still at 5° C. for 30 minutes. The precipitated crystals were filtered by suction, washed with isopropyl ether (120 ml) and dried to give 6-fluoro-2-(2-nitroanilino)benzo[b]thiophene-3-carbonitrile (8.0 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated crystals were filtered by suction
  3. washwashed with isopropyl ether (120 ml)
  4. customdried

Sources & evidence

ORD record
ord-4320b5667d21494aa0c7054b5d3606a8
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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