Sodium Hydroxide → HCID 21527312, compound

HRID 1658379Notes

Reaction equation

HRID 1658379 reaction equation
C(O)(=O)/C=C/C(O)=O.[CH:9]1([N:15]2[CH2:19][CH2:18][CH:17]([N:20]([CH3:32])[C:21](=O)[C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+].[S-2:35].[K+].[K+]>C1C=CC=CC=1>[CH:9]1([N:15]2[CH2:19][CH2:18][CH:17]([N:20]([CH3:32])[C:21](=[S:35])[C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 162263Potassium SulfideHCID 12895720HCID 12895720, compound

Product 1

HCID 21527312HCID 21527312, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Twenty-five grams (0.56 mole) of N-(1-cyclohexyl-3-pyrrolidinyl)-p-nitro-N-methylbenzamide fumarate was partitioned between dil. sodium hydroxide and 400 ml. benzene. The benzene solution was dried with sodium sulfate and distilled to a volume of 250 ml. To this was added a finely ground mixture of 10 g. (0.045 mole) of phosphorous pentasulfide and 10 g. of potassium sulfide. The mixture was refluxed 4 hours and an additional 10 g. of phosphorous pentasulfide added and refluxed 2 hours. The benzene was decanted off of the hard solid. The solid was partitioned between dil. sodium hydroxide and chloroform. The chloroform was dried, concentrated and the residue crystallized twice from isopropyl ether-ethyl acetate. Yield 3.77 g. (19.5%); m.p. 108°-110°C.

Workup

  1. dry with materialThe benzene solution was dried with sodium sulfate
  2. distillationdistilled to a volume of 250 ml
  3. additionTo this was added
  4. additiona finely ground mixture of 10 g
  5. temperatureThe mixture was refluxed 4 hours
  6. temperaturerefluxed 2 hours
  7. customThe benzene was decanted off of the hard solid
  8. customThe solid was partitioned between dil. sodium hydroxide and chloroform
  9. dry with materialThe chloroform was dried
  10. concentrationconcentrated
  11. customthe residue crystallized twice from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-93b75fb95cf4433f8487c61829559be4
Source dataset
uspto-grants-1976_06
Patent number
US03963745

Reaction notes

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