HCID 68729025, compound → HCID 68724254, compound

HRID 1892059Notes

Reaction equation

HRID 1892059 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9](C(O)=O)=[CH:10][C:6]=2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

4

Reactant 1

HCID 68729025HCID 68729025, compound

Product 1

HCID 68724254HCID 68724254, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
200 °C

Procedure

To the suspension of acid (12.9 g, 0.05 mol) from step 2 in quinoline (200 ml) was added copper powder (5.2 g, 0.08 mol) and the mixture was heated at 200° C. for 2 h. The reaction mixture was cooled and extracted in ether. The ethereal layer was washed with 50% HCl, brine and dried over sodium sulphate and concentrated to yield 7-chloro-5-nitro-benzo[b]thiophene, 6.2 g which was used as such in Step 4, MS m/z 213 (M+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted in ether
  3. washThe ethereal layer was washed with 50% HCl, brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac9960e16f80475fb324c991a37f20cc
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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