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

HRID 1816236Notes

Reaction equation

HRID 1816236 reaction equation
NC1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(O)(=O)C>[OH-].[Na+]>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:4]=1[SH:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 3199542-Amino-6-fluorobenzothiazole

Product 1

HCID 3205472-Amino-5-fluorobenzene-1-thiolYield 129.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

2-Amino-6-fluorobenzothiazole (5.0 g, 29.7 mmol) was stirred in 10N NaOH (120 mL) and heated to 120° C. After 2 hours the mixture was allowed to cool and treated with acetic acid (˜70 mL) to adjust the pH of the mixture to 4.0. The resulting precipitate was collected and washed with 3 volumes (30 mL) of water and dried in vacuo to give 5.5 g of 2-amino-5-fluorothiophenol suitable for use in the subsequent step.

Workup

  1. temperatureto cool
  2. customThe resulting precipitate was collected
  3. washwashed with 3 volumes (30 mL) of water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cfe81221548548d3a409eaf7c68cb021
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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