Acetic Acid → HCID 69514021, compound

HRID 858143Notes

Reaction equation

HRID 858143 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[S:8]C#N.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].C(O)(=O)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[SH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73972Sodium sulfide nonahydrate2×HCID 713621512-Bromo-4-hydroxyphenyl thiocyanate

Product 1

HCID 69514021HCID 69514021, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a hot (85° C.) solution of 3-bromo-4-thiocyanato-phenol (315 mg, 1.37 mmol) in absolute ethanol (10 mL) under nitrogen, sodium sulfide nonahydrate (403 mg, 2.05 mmol) was added. The resulting mixture was stirred at 85° C. for 20 min. More sodium sulfide nonahydrate (230 mg) was added and heating was continued for 15 min. The mixture was cooled down, made acidic with 5N acetic acid (10 mL) and extracted with methylene chloride (×1). The organic layer was washed once with water, dried and concentrated in vacuo to give the title compound as a yellow solid (259 mg, 92%) which was quickly submitted to the next reaction without further treatment. EIMS M−1: 203.

Workup

  1. temperatureheating
  2. waitwas continued for 15 min
  3. temperatureThe mixture was cooled down
  4. extractionextracted with methylene chloride (×1)
  5. washThe organic layer was washed once with water
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c171be188214721b2b5031767d87b28
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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