Phosphorus sulfide (P2S5) → HCID 23453664, compound

HRID 1277368Notes

Reaction equation

HRID 1277368 reaction equation
[C:1]1([CH:7]2[C:14]3([CH2:18][CH2:17][C:16](=O)[NH:15]3)[CH:11]3[CH2:12][CH2:13][CH:8]2[CH2:9][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].[O-2].[Ca+2]>C1(C)C=CC=CC=1>[C:1]1([CH:7]2[C:14]3([CH2:18][CH2:17][C:16](=[S:21])[NH:15]3)[CH:11]3[CH2:12][CH2:13][CH:8]2[CH2:9][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 6850728CalciumoxideHCID 23453765HCID 23453765, compound

Product 1

HCID 23453664HCID 23453664, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

33 mmoles of 3-phenyl-spiro[bicyclo[2.2.2]-octane-2,2'-pyrrolidin]-5'-one are dispersed in 200 ml of toluene, and a mixture of 7.3 g of phosphorus pentasulfide and 7 g of calcium oxide is added, whilst stirring, and the mixture is stirred at 50° C. for 21/2 hours. The hot reaction solution is filtered into a saturated sodium carbonate solution. The residues are dissolved in concentrated hydrochloric acid and the solution is diluted with water and carefully combined with the toluene/sodium carbonate mixture. The aqueous phase is extracted several times with toluene and the extracts are combined, dried and concentrated in vacuo. Recrystallization of the residue from a little ethyl acetate gives colorless crystals.

Workup

  1. additionis added
  2. stirringthe mixture is stirred at 50° C. for 21/2 hours
  3. filtrationThe hot reaction solution is filtered into a saturated sodium carbonate solution
  4. dissolutionThe residues are dissolved in concentrated hydrochloric acid
  5. additionthe solution is diluted with water
  6. extractionThe aqueous phase is extracted several times with toluene
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customRecrystallization of the residue from a little ethyl acetate
  10. customgives colorless crystals

Sources & evidence

ORD record
ord-4fed30f9b90d491ba600b6ce85093316
Source dataset
uspto-grants-1981_07
Patent number
US04277470

Reaction notes

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