Sodium Hydroxide → HCID 14922563, compound

HRID 1189131Notes

Reaction equation

HRID 1189131 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:12]2[S:11]C(N)=[N:9][C:8]=2[C:7]([CH3:14])=[CH:6][CH:5]=1>C(O)CO>[NH2:9][C:8]1[C:7]([CH3:14])=[CH:6][CH:5]=[C:4]([Cl:3])[C:12]=1[SH:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20498937-chloro-4-methyl-benzothiazol-2-ylamine

Product 1

HCID 14922563HCID 14922563, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of NaOH (10N, 8.0 mL) was added 7-chloro-4-methyl-benzothiazol-2-ylamine (530 mg, 2.67 mmol) and ethylene glycol (10 mL) then the reaction mixture was stirred at 150° C. for 1 day. After being cooled down, the reaction mixture was filtered. The filtrate was extracted with DCM. The aqueous phase was acidified with HCl 1N and extracted with DCM. Then, the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated to yield 2-amino-6-chloro-3-methyl-benzenethiol (252 mg, 1.45 mmol, 54%) as a yellow oil.

Workup

  1. temperatureAfter being cooled down
  2. filtrationthe reaction mixture was filtered
  3. extractionThe filtrate was extracted with DCM
  4. extractionextracted with DCM
  5. washThen, the combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4bfb0515bcd74bf586a035a6a38d1acc
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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