Sodium → HCID 13035279, compound

HRID 434555Notes

Reaction equation

HRID 434555 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([NH:10][C:11]([NH:13][CH2:14][CH2:15][OH:16])=S)[C:2]1=2.[Na]>C(O)C.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[O:16]1[CH2:15][CH2:14][N:13]=[C:11]1[NH:10][C:9]1[C:2]2[O:1][CH:5]=[CH:4][C:3]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 13035278HCID 13035278, compound

Product 1

HCID 13035279HCID 13035279, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 702EthanolSolvent2×

Procedure

5.4 g of N-benzo[b]furan-7-yl-N'-2-hydroxyethylthiourea in 300 ml of ethanol are boiled under reflux and are treated with a solution of 1.12 g of sodium in 25 ml of ethanol. The hot mixture is treated with 8.1 g of mercury(II) acetate over 1/2 minute, refluxed for 15 minutes and then filtered. The filtrate is evaporated to dryness. The residue is partitioned between 40 ml of 1 N hydrochloric acid and 40 ml of methylene chloride. The aqueous phase is treated with active charcoal, filtered and made alkaline with concentrated ammonia solution. The resultant precipitate is filtered, dried and recrystallised from ethyl acetate to give the title compound in free base form. M.Pt. 124°-6°.

Workup

  1. temperatureunder reflux
  2. temperaturerefluxed for 15 minutes
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customThe residue is partitioned between 40 ml of 1 N hydrochloric acid and 40 ml of methylene chloride
  6. additionThe aqueous phase is treated with active charcoal
  7. filtrationfiltered
  8. filtrationThe resultant precipitate is filtered
  9. customdried
  10. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-5d397c067fd14abeae1afeabf723cd6f
Source dataset
uspto-grants-1983_08
Patent number
US04398028

Reaction notes

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