2-[(3-Methyl-4-nitrophenoxy)methyl]-1,3-benzothiazole → 4-(Benzo(D)Thiazol-2-Ylmethoxy)-2-Methylaniline

HRID 1597807Notes

Reaction equation

HRID 1597807 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([CH3:21])[CH:13]=1>O1CCCC1.[Pt]=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([CH3:21])[CH:13]=1

Participants

4

Reactant 1

HCID 9353992-[(3-Methyl-4-nitrophenoxy)methyl]-1,3-benzothiazole

Product 1

HCID 9354004-(Benzo(D)Thiazol-2-Ylmethoxy)-2-MethylanilineYield 101.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of platinum oxide were added to a solution of 35.0 g of O-(benzothiazol-2-ylmethyl)-3-methyl-4-nitrophenol [prepared as described in step (a) above] in 500 ml of tetrahydrofuran at room temperature and the mixture was vigorously stirred under a hydrogen atmosphere for 2 hours. At the end of this time, the reaction mixture was filtered through Celite™ and the resulting filtrate was concentrated by evaporation under reduced pressure to give a crude residue which was washed with diisopropyl ether to give 32.1 g (yield 100%) of the title compound as a solid having a melting point of 110° to 111° C.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered through Celite™
  2. concentrationthe resulting filtrate was concentrated by evaporation under reduced pressure
  3. customto give a crude residue which
  4. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-5190eb6830ab44358513afa9141dda23
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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