Benzene → 1-(1-Methyl-2-pyrrolidylidene)-3-o-tolyl urea

HRID 2071528Notes

Reaction equation

HRID 2071528 reaction equation
Cl.[NH:2]=[C:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH3:8].C1C=CC=CC=1.[OH-].[Na+].[C:17]1([CH3:26])[C:18]([N:23]=[C:24]=[O:25])=[CH:19][CH:20]=[CH:21][CH:22]=1>O>[CH3:8][N:4]1[CH2:5][CH2:6][CH2:7][C:3]1=[N:2][C:24]([NH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH3:26])=[O:25]

Participants

6

Reactant 4

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 691942-Tolyl isocyanateHCID 124489671-Methylpyrrolidin-2-imine hydrochloride

Product 1

HCID 536542301-(1-Methyl-2-pyrrolidylidene)-3-o-tolyl urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 6.73 g. (0.05 mole) sample of 2-imino-1-methylpyrrolidine HCl is treated with 50 ml. of benzene and 2 ml. of water. With stirring, 10 ml. of 50% sodium hydroxide is added. After stirring about one minute, the benzene layer is decanted onto anhydrous K2CO3 and the extraction repeated twice with 50 ml. portions of benzene. The dried, combined extracts are filtered from the drying agent and the filtrate is treated with 6.66 g. (0.05 mole) of o-tolylisocyanate. After stirring overnight, the mixture is filtered from a small amount of insoluble material and the solvent removed in vacuo. Recrystallization from ethyl acetate and finally from ether gives the pure product, 1-(1-methyl-2-pyrrolidylidene)-3-o-tolyl urea. m.p. = 91°-93° C.

Workup

  1. stirringAfter stirring about one minute
  2. customthe benzene layer is decanted onto anhydrous K2CO3
  3. extractionthe extraction
  4. filtrationare filtered from the drying agent
  5. additionthe filtrate is treated with 6.66 g
  6. stirringAfter stirring overnight
  7. filtrationthe mixture is filtered from a small amount of insoluble material
  8. customthe solvent removed in vacuo
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b561b55b08bb46539a562f8044ddb681
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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