Toluene → HCID 13726444, compound

HRID 236166Notes

Reaction equation

HRID 236166 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[Cl:15][CH2:16][CH2:17][C@@H:18]1[CH2:24][N:23]([CH3:25])[C:22](=O)[C:21]2[CH:27]=[CH:28][CH:29]=[N:30][C:20]=2[O:19]1.C1(C)C=CC=CC=1>C(#N)C>[Cl:15][CH2:16][CH2:17][C@@H:18]1[CH2:24][N:23]([CH3:25])[C:22](=[S:2])[C:21]2[CH:27]=[CH:28][CH:29]=[N:30][C:20]=2[O:19]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14817Phosphorus sulfide (P2S5)HCID 13726439HCID 13726439, compound

Product 1

HCID 13726444HCID 13726444, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 9 g (0.02 mole) of phosphorus pentasulfide in 75 ml of acetonitrile was added 18 g (0.075 mole) of (R)-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-one and the mixture was stirred at reflux for 2.5 hr, cooled and treated with 60 ml of toluene. The mixture was filtered and the solid washed twice with 30 ml of 25% acetonitrile-75% toluene. The volume was made to about 400 ml with 50% toluene-50% acetonitrile and extracted with saturated aqueous potassium bicarbonate. The organic layer was separated, treated with magnesium sulfate and charcoal, and filtered. The filtrate was concentrated and the residue was recrystallized from isopropyl alcohol-chloroform. Yield of title compound was 13 g (68%), m.p. 168°-170° C.; [α]D25 =(-) 47.4 (chloroform).

Workup

  1. temperatureat reflux for 2.5 hr
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. washthe solid washed twice with 30 ml of 25% acetonitrile-75% toluene
  5. extractionextracted with saturated aqueous potassium bicarbonate
  6. customThe organic layer was separated
  7. additiontreated with magnesium sulfate and charcoal
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe residue was recrystallized from isopropyl alcohol-chloroform

Sources & evidence

ORD record
ord-8f9ec6a5a4604925ae33ee86fb19cf05
Source dataset
uspto-grants-1987_02
Patent number
US04642343

Reaction notes

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