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

HRID 1489131Notes

Reaction equation

HRID 1489131 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-2b027d7f9da2408bb74ad37c7bd04a08
Source dataset
uspto-grants-1997_10
Patent number
US05677321

Reaction notes

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