HCID 7854344, compound → HCID 23296465, compound

HRID 1954392Notes

Reaction equation

HRID 1954392 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:5][CH:4]=1)#[N:2]>C(O)(=O)C.[Fe]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][S:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 7854344HCID 7854344, compound

Product 1

HCID 23296465HCID 23296465, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 1.0 g (3.05 mmol) of 2-[(4-cyanophenyl)methylthio]-6-nitro-benzothiazole is heated to boiling in 60 ml glacial acetic acid until a clear solution is formed. Then 2.0 g (36 mmol) of iron powder is added in two batches and the resulting mixture is refluxed for 5 minutes. It is filtered, and the filtrate is concentrated in vacuo. The crude product is made alkaline by the addition of conc. ammonia and purified by flash chromatography (silica gel, ethyl acetate/petroleum ether=20:80 to 35:65).

Workup

  1. temperatureis heated
  2. customis formed
  3. temperaturethe resulting mixture is refluxed for 5 minutes
  4. filtrationIt is filtered
  5. concentrationthe filtrate is concentrated in vacuo
  6. additionby the addition of conc. ammonia
  7. custompurified by flash chromatography (silica gel, ethyl acetate/petroleum ether=20:80 to 35:65)

Sources & evidence

ORD record
ord-4f962aedb72d4903ad76b84fd412e00b
Source dataset
uspto-grants-2000_09
Patent number
US06121308

Reaction notes

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