Hydrochloric Acid → HCID 22610083, compound

HRID 2306667Notes

Reaction equation

HRID 2306667 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[C:6]([SH:8])[CH:7]=1.[C:10](OCC)(=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].O.Cl>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:8][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7268Diethyl OxalateHCID 3205472-Amino-5-fluorobenzene-1-thiol

Product 1

HCID 22610083HCID 22610083, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-fluoro-2-aminobenzenethiol (0.94 g, 6.6 mmol) in diethyl oxalate (1.8 mL, 13 mmol) is heated at reflux for overnight. The solution is poured into a mixture of water (9.8 mL), conc. HCl (3.3 mL), and EtOH (4.6 mL). The material is extracted with CHCl3 (3×100 mL). The combined organic extracts are dried over MgSO4, filtered and concentrated to yield an oil. The material is purified by chromatography (25% hexanes/75% CHCl3) to afford a solid that is recrystallized from petroleum ether (0.16 g, 11%). MS for C10H8NO2SF: m/z 226 (M+H)+.

Workup

  1. temperatureat reflux for overnight
  2. extractionThe material is extracted with CHCl3 (3×100 mL)
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield an oil
  7. customThe material is purified by chromatography (25% hexanes/75% CHCl3)
  8. customto afford a solid
  9. customthat is recrystallized from petroleum ether (0.16 g, 11%)

Sources & evidence

ORD record
ord-8ad1bdf8bc0d4347b3048d09e24d4f0f
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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