Sodium Hydroxide → HCID 21527312, compound

HRID 1659156Notes

Reaction equation

HRID 1659156 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 four hours and an additional 10 g. of phosphorous pentasulfide added and refluxed two 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 four hours
  6. temperaturerefluxed two 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-a85747473c504c58898f5277c529667e
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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