Nitrogen → HCID 21218650, compound

HRID 1585536Notes

Reaction equation

HRID 1585536 reaction equation
N#N.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][N:13]([CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17]O)[C:12](=O)[C:11]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][CH:5]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:29]>[OH-].[Na+]>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:12]3[N:13]([CH:14]=2)[CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][S:29]3)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 14817Phosphorus sulfide (P2S5)HCID 21218646HCID 21218646, compound

Product 1

HCID 21218650HCID 21218650, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

At a 170-180° C. bath temperature, in a protective atmosphere of N2, 4-(4-chlorophenyl)-1-(2,2-dimethyl-3-hydroxypropyl)-3-phenyl-1,5-dihydro-pyrrol-2-on (5, 10.7 g, 0.03 mol) is melted with phosphorus pentasulfide (3.33 g, 2.5 equiv., 0.015 mol), which is added in small portions until the gas development comes to a halt (1 h). Then the cooled reaction mixture is akalyzed with caustic soda (100 mL, 10%) and extracted with chloroform; the organic phase is washed with water and dried. The residue remaining after the evaporation of chloroform is crystallized from diisopropyl ether having a melting point of 147-148° C. (5.5 g, 52%).

Workup

  1. additionis added in small portions until the gas development
  2. customcomes to a halt (1 h)
  3. customThen the cooled reaction mixture
  4. extractionextracted with chloroform
  5. washthe organic phase is washed with water
  6. customdried
  7. customafter the evaporation of chloroform
  8. customis crystallized from diisopropyl ether having a melting point of 147-148° C. (5.5 g, 52%)

Sources & evidence

ORD record
ord-a0e40e355ed44401992631e27417badf
Source dataset
uspto-grants-1999_08
Patent number
US05939415

Reaction notes

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