Sodium Hydroxide → HCID 3039360, compound

HRID 1973925Notes

Reaction equation

HRID 1973925 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[OH-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([N:17]=[C:18]=[O:19])[CH:14]=[CH:15][CH:16]=1>C1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:19])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 3039360HCID 3039360, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Assuming 100 % conversion, 2.94 g. (0.03 mole) of 2 -imino-1 -methylpyrrolidine is liberated from its HCL salt using the calculated amount of 50 % NaOH (2.4 g., 0.03 mole) and extracting into benzene. The benzene solution is dried over K2CO3. To this solution, 4.6 g. (0.03 mole) of m-chlorophenylisocyanate dissolved in anhydrous benzene is added dropwise with stirring. Solid forms and the mixture is stirred at room temperature overnight. The solid, 1 -m-chlorophenyl-3 -(1 -methyl-2 -pyrrolidylidene)urea, is collected, m.p. = 135°-136° C. A second crop is collected from the mother liquors after taking it to dryness, triturating with hot CHCl3, and filtering off that which does not dissolve. The two crops are combined and recrystallized from methanol-ether to give the pure product, m.p. = 137°-138° C.

Workup

  1. extractionextracting into benzene
  2. dry with materialThe benzene solution is dried over K2CO3
  3. additionis added dropwise
  4. stirringSolid forms and the mixture is stirred at room temperature overnight
  5. customThe solid, 1 -m-chlorophenyl-3 -(1 -methyl-2 -pyrrolidylidene)urea, is collected
  6. customA second crop is collected from the mother liquors
  7. customtriturating with hot CHCl3
  8. filtrationfiltering off that which
  9. dissolutiondoes not dissolve
  10. customrecrystallized from methanol-ether
  11. customto give the pure product, m.p. = 137°-138° C.

Sources & evidence

ORD record
ord-bf62f9cb399c4121902817b0c34ce793
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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