Ammonia → HCID 10845577, compound

HRID 265301Notes

Reaction equation

HRID 265301 reaction equation
[Ca].N.[C:3]1([CH2:9][CH:10]2[S:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOCC>[C:3]1([CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][SH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5460341CalciumHCID 123959182-Benzyl-1,3-oxathiane

Product 1

HCID 10845577HCID 10845577, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Calcium turnings (3.5 g) were added portionwise to liquid ammonia (500 ml) and the whole was stirred vigorously for 10 min. The thioacetal from step b) (10 g) in ether (7 ml) was added dropwise to the dark blue solution over a 7 min period. The mixture was stirred for 2 hours and then quenched with ammonium chloride until effervescing had ceased. Excess ammonia was allowed to evaporate by purging under nitrogen overnight. The remaining solid was acidified using dilute 10% aqueous hydrochloric acid to pH 1-2 and the product extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give the subtitled compound (8.29 g).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customquenched with ammonium chloride until effervescing
  3. customto evaporate
  4. customby purging under nitrogen overnight
  5. additionThe remaining solid was acidified using dilute 10% aqueous hydrochloric acid to pH 1-2
  6. extractionthe product extracted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae24317e5e714fea8e0d25c52741612d
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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