HCID 86049181, compound → HCID 86049183, compound

HRID 2235484Notes

Reaction equation

HRID 2235484 reaction equation
[C:1]1([CH3:22])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1>C(O)(=O)C.C(O)C.[Fe]>[C:1]1([CH3:22])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 1

HCID 86049181HCID 86049181, compound

Product 1

HCID 86049183HCID 86049183, compoundYield 55.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 1.8 g (5.7 mmol) of N2-mesityl-7-nitro-1,3-benzothiazol-2-amine in 7.2 mL of glacial acetic acid and 25 mL of ethanol was added 1.8 g (32 mmol) of iron powder. The resulting solution was heated at reflux for 18 h before being cooled to room temperature. The slurry was filtered and the filtrate was concentrated to a brown solid. The solid was slurried in water, collected by filtration and purified by flash chromatography eluting with a 33% hexanes/ethyl acetate mixture to give 0.9 g (55%) of the title compound as a tan powder.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 h
  3. filtrationThe slurry was filtered
  4. concentrationthe filtrate was concentrated to a brown solid
  5. filtrationcollected by filtration
  6. custompurified by flash chromatography
  7. washeluting with a 33% hexanes/ethyl acetate mixture

Sources & evidence

ORD record
ord-dc6d4e4c234a43b297d72482043d6d14
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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