Hydrochloric Acid → HCID 69514074, compound

HRID 858144Notes

Reaction equation

HRID 858144 reaction equation
[S:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:16])=[CH:6][CH:5]=1)C#N.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].Cl>C(O)C>[SH:1][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 85868919HCID 85868919, compound

Product 1

HCID 69514074HCID 69514074, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-thiocyanato-biphenyl-2-ol (160 mg, 0.97 mmol) in absolute ethanol (8 mL) under nitrogen, sodium sulfide nonahydrate (298 mg, 1.1 6 mmol) was added. The resulting mixture was stirred at 85° C. for 20 min. The mixture was cooled down, made acidic with 10% aqueous HCl and extracted with ethyl acetate (×2). The combined organic layers were dried on MgSO4 and concentrated in vacuo to give the title compound as a yellow solid (105 mg, 95%) which was quickly submitted to the next reaction without further purification.

Workup

  1. temperatureThe mixture was cooled down
  2. extractionextracted with ethyl acetate (×2)
  3. customThe combined organic layers were dried on MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8cd73468280455fa48ed91fa3019f00
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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