Ammonia → HCID 18943079, compound

HRID 400276Notes

Reaction equation

HRID 400276 reaction equation
N.C(OCC)C.C([S:14][C:15]1[C:16](=[O:30])[CH:17]=[C:18]([S:22]CC2C=CC=CC=2)[C:19](=[O:21])[CH:20]=1)C1C=CC=CC=1.[Na]>C(O)C>[SH:14][C:15]1[CH:20]=[C:19]([OH:21])[C:18]([SH:22])=[CH:17][C:16]=1[OH:30]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 5360545SodiumHCID 54305778HCID 54305778, compound

Product 1

HCID 18943079HCID 18943079, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ammonia was condensed (ca 200 ml) into 150 ml of dry diethylether in a 3-necked flask, with external cooling. Then 9.0 g (0.0256 mole) of 2,5-dibenzylmercapto-p-benzoquinone was dissolved into the liquid. Sodium (5.9 g, 0.256 mole) cut into fine pieces was added portionwise with efficient stirring. After stirring for an additional 2.5 hours, abs. ethanol (20 ml) was added and the ammonia was evaporated. Water (170 ml) was added to the reaction product and it was extracted with 2×30 ml of ether. The aqueous phase was then acidified to pH 1-2, with conc. hydrochloric acid, and extracted with 3×80 ml of ether. The ether extracts were collected, dried (Na2SO4), the solvent evaporated leaving a fluffy light brown glistening residue, 4.3 g (90%).

Workup

  1. additionwas added portionwise with efficient stirring
  2. customthe ammonia was evaporated
  3. additionWater (170 ml) was added to the reaction product and it
  4. extractionwas extracted with 2×30 ml of ether
  5. extractionextracted with 3×80 ml of ether
  6. customThe ether extracts were collected
  7. dry with materialdried (Na2SO4)
  8. customthe solvent evaporated
  9. customleaving a fluffy light

Sources & evidence

ORD record
ord-01f49e24e7df48e08719701fcc7ca44e
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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