Acetic Acid → 2-Amino-5-methoxybenzene-1-thiol

HRID 1960161Notes

Reaction equation

HRID 1960161 reaction equation
NC1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.C(O)(=O)C>[OH-].[K+]>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([SH:3])[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 156302-Amino-6-methoxybenzothiazole

Product 1

HCID 2355092-Amino-5-methoxybenzene-1-thiolYield 95%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2-Amino-6-methoxy-benzothiazole 10 g (55.6 mmol) was suspended in 25% aqueous potassium hydroxide and the mixture heated under reflux for 24 h. The pale yellow solution was cooled and acidified to pH 6 with firstly aqueous 6N HCl then acetic acid. The precipitated solid was filtered, washed with water (3×100 ml), dried (high vac.) to afford the desired material as a pale yellow powder 8.18 g, 95%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 24 h
  3. temperatureThe pale yellow solution was cooled
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water (3×100 ml)
  6. customdried (high vac.)

Sources & evidence

ORD record
ord-d639e5ef42774ad3b62a7bcb18e32c65
Source dataset
uspto-grants-2013_04
Patent number
US08410312B2

Reaction notes

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