Sodium Hydroxide → Benzothiazol-5-amine

HRID 1936592Notes

Reaction equation

HRID 1936592 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-])=O.[OH-].[Na+]>CC(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3501355-Nitrobenzothiazole

Product 1

HCID 70749Benzothiazol-5-amineYield 84.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3.46 g of 5-nitrobenzothiazole and 15.7 g of stannous chloride dihydrate in 55 mL of 2-propanol is heated to reflux for 3 hours. The cooled reaction mixture is poured into 150 mL of ice/water and neutralized to pH 7 using solid sodium hydroxide. The mixture is extracted with ethyl acetate (3×50 mL). The combined organic layers are dried over sodium sulfate, filtered through a short pad of silica gel, and rotary evaporated to provide 2.45 g of 5-aminobenzothiazole as a yellow-brown solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 hours
  3. customThe cooled reaction mixture
  4. extractionThe mixture is extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered through a short pad of silica gel
  7. customrotary evaporated

Sources & evidence

ORD record
ord-2f5f9684b83649d7b4639c05b74a5993
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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