Potassium Hydroxide → 2-Amino-5-fluorobenzene-1-thiol

HRID 396945Notes

Reaction equation

HRID 396945 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=C(N)[S:10][C:6]=2[CH:5]=1.[K]>O>[NH2:8][C:7]1[CH:12]=[CH:13][C:4]([F:3])=[CH:5][C:6]=1[SH:10]

Participants

5

Conditions

Temperature
40 °C

Procedure

In a 2,000-ml flask as a reactor were placed 166.7 g of water, 589.3 g of a 50% aqueous potassium hydroxide solution (5.25 moles as KOH) and 168.2 g (1.00 mole) of 6-fluoro-2-aminobenzothiazole. They were heated, aged for 8 hours with refluxing at 113 to 115° and then cooled to 40° C. The resulting mixture was washed with 311 g of toluene and then subjected to phase separation to obtain 904.0 g of an aqueous solution of a potassium salt of 2-amino-5-fluorothiophenol (concentration: 20%, yield: 99.7%). This aqueous solution of a potassium salt of 2-amino-5-fluorothiophenol can be used for production of a p-toluenesulfonate of [2-(6-fluorobenzothiazolyl)]ethylamine or an aqueous solution of [2-(6-fluorobenzothiazolyl)]ethylamine hydrochloride, according to the description in Example 1 to Example 7.

Workup

  1. customIn a 2,000-ml flask as a reactor were placed
  2. temperatureThey were heated
  3. temperaturewith refluxing at 113 to 115°
  4. washThe resulting mixture was washed with 311 g of toluene
  5. customsubjected to phase separation

Sources & evidence

ORD record
ord-7c12c43c14d14233ae761aedcae91568
Source dataset
uspto-grants-2003_08
Patent number
US06608207B2

Reaction notes

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