2(3H)-benzothiazolone, 3-methyl-6-nitro- → HCID 10442296, compound

HRID 723844Notes

Reaction equation

HRID 723844 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[N:8]([CH3:12])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-])=O.[H][H]>CO.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[N:8]([CH3:12])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 6415702(3H)-benzothiazolone, 3-methyl-6-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 10442296HCID 10442296, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-nitro-3-methyl-2-benzothiazolinone (J. Heterocyclic Chem. 1992, 29, 1069–1076, 4.85 g, 23.1 mmol) and 10% palladium-on-carbon (491 mg, 0.461 mmol) in a mixture of MeOH (45 mL) and tetrahydrofuran (45 mL) is shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 17 h. The catalyst is removed by filtration through a pad of Celite, and the filtrate is concentrated under reduced pressure and triturated with ethyl acetate/hexanes. Filtration then provides the title compound, mp 188–190° C.; MS (ESI+) for C8H8N2OS m/z 181 (M+H)+.

Workup

  1. customThe catalyst is removed by filtration through a pad of Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customtriturated with ethyl acetate/hexanes
  4. filtrationFiltration

Sources & evidence

ORD record
ord-3712b5a390b641f69601da860d3d48c9
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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