Sodium Hydroxide → 6-Methylbenzo[d]thiazol-5-amine

HRID 1936590Notes

Reaction equation

HRID 1936590 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[OH-].[Na+]>C(O)C.[Cl-].[Na+].O>[NH2:11][C:10]1[C:2]([CH3:1])=[CH:3][C:4]2[S:8][CH:7]=[N:6][C:5]=2[CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 224622156-Methyl-5-nitrobenzothiazole

Product 1

HCID 224622166-Methylbenzo[d]thiazol-5-amineYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 0.78 g of 6-methyl-5-nitrobenzothiazole and 3.62 g of stannous chloride dihydrate in 25 mL of ethanol is heated to 65° C. for 4 hours. The cooled reaction mixture is poured into 10 mL of 50% sodium hydroxide and 45 mL of brine and extracted with ether (4×35 mL). The combined organic layers are washed with brine, dried over sodium sulfate and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 15% ethyl acetate/hexanes to provide 0.45 g of 5-amino-6-methylbenzothiazole as a yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ether (4×35 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate and rotary evaporated
  5. customThe residue is purified by flash column chromatography on silica gel
  6. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-85269b1705484467bd7466db3d59b796
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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