Benzene → HCID 53654230, compound

HRID 1973956Notes

Reaction equation

HRID 1973956 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 53654230HCID 53654230, compound

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 K 2 CO 3 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 K 2 CO 3
  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-10e93bd9fe2143cfaa270185382eefc1
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

Loading…