Sodium Hydroxide → 7-Methylbenzo[d]thiazol-5-amine

HRID 617271Notes

Reaction equation

HRID 617271 reaction equation
Cl[Sn]Cl.[CH3:4][C:5]1[C:13]2[S:12][CH:11]=[N:10][C:9]=2[CH:8]=[C:7]([N+:14]([O-])=O)[CH:6]=1.[OH-].[Na+]>Cl>[CH3:4][C:5]1[C:13]2[S:12][CH:11]=[N:10][C:9]=2[CH:8]=[C:7]([NH2:14])[CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 227280277-Methyl-5-nitro-1,3-benzothiazole

Product 1

HCID 227280287-Methylbenzo[d]thiazol-5-amineYield 570.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2 (1.5 g, 1.9 mmol) in 5.0 mL of HCl was added 7-methyl-5-nitrobenzothiazole (65 m g, 0.32 mmol) in a portion and resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc and CHCl3. Combined organic layers were dried over Na2SO4 and concentrated in vacuo, yielding an oil (0.30 g, >95%) which was identified as the desired amine (>95% pure) and subjected to the following reaction without further purification.

Workup

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with EtOAc and CHCl3
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-151f69a8862a4d99afc0fe15281a2a49
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Reaction notes

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