Carbon Disulfide → 5-Fluorobenzoxazole-2-thiol

HRID 70126Notes

Reaction equation

HRID 70126 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[K+].[C:12](=S)=[S:13]>CCO>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:12](=[S:13])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 27359172-Amino-4-fluorophenol

Product 1

HCID 107972085-Fluorobenzoxazole-2-thiol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-fluorophenol (1.21 g, 9.52 mmol) and potassium hydroxide (0.64 g, 11.4 mmol) were dissolved in carbon disulfide (15 mL) and EtOH (25 mL), and the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The resulting solid was suspended in 1 M aqueous HCl and collected by filtration. This was washed with 1 M aqueous HCl (2×) and water (2×) and was air-dried. This gave 1.115 g (69%) of the title compound as a yellow solid. LC-MS: RT=6.89 min., [M+H]+=169.9.

Workup

  1. temperatureto reflux overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. filtrationcollected by filtration
  4. washThis was washed with 1 M aqueous HCl (2×) and water (2×)
  5. customwas air-dried

Sources & evidence

ORD record
ord-c673d7e01faa4150a637bcd8bf947dcf
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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