Phosphorus sulfide (P2S5) → HCID 22865603, compound

HRID 744169Notes

Reaction equation

HRID 744169 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[C:15]([O:23][C@H:24]1[C@@H:28]([O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:27]([CH2:38][O:39][C:40](=[O:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:26][C@H:25]1[N:48]1[CH:55]=[CH:54][C:52](=O)[NH:51][C:49]1=[O:50])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:15]([O:23][C@H:24]1[C@@H:28]([O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:27]([CH2:38][O:39][C:40](=[O:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:26][C@H:25]1[N:48]1[CH:55]=[CH:54][C:52](=[S:2])[NH:51][C:49]1=[O:50])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 67746080HCID 67746080, compound

Product 1

HCID 22865603HCID 22865603, compoundYield 95.5%

Procedure

Phosphorus pentasulfide (5.99 g, 26.95 mmol) was added to a solution of compound 18 (3.75 g, 6.73 mmol) inpyridine (70 ml) and was refluxed for four hours. After cooling, the solvent was evaporated and the residue dissolved in CHCl3, washed with water and brine. After drying over anhydrous Na2SO 4, evaporation of the solvent gave the crude product which was purified on a silica gel column using 30% EtOAc/petroleum ether as solvent to give compound 19 (3.68 g, 95%) as golden yellow foam.

Workup

  1. temperaturewas refluxed for four hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. dissolutionthe residue dissolved in CHCl3
  5. washwashed with water and brine
  6. dry with materialAfter drying over anhydrous Na2SO 4, evaporation of the solvent
  7. customgave the crude product which
  8. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-7db2a723e51e42c2839dbc0bff529605
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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