Sodium Hydroxide → 1-(1-Methylpyrrolidin-2-ylidene)-3-(p-nitrophenyl)urea

HRID 2071491Notes

Reaction equation

HRID 2071491 reaction equation
Cl.[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[NH:8].[OH-].[Na+].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1)([O-:13])=[O:12].[N-]=C=O>C1C=CC=CC=1.O>[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[N:8][C:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=1)=[O:22]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 105034IsocyanateHCID 124489671-Methylpyrrolidin-2-imine hydrochloride

Product 1

HCID 30393631-(1-Methylpyrrolidin-2-ylidene)-3-(p-nitrophenyl)urea

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 6.73 g. (0.05 mole) of 1-methyl-2-iminopyrrolidine hydrochloride in 100 ml. of benzene is added 2 ml. of water followed by 5 ml. of 50% NaOH. After stirring for 5 min., the benzene layer is decanted onto excess anhydrous potassium carbonate. The process is repeated twice with 75 ml. portions of fresh benzene. The combined extracts are filtered rapidly from drying agent (dicalite pad and suction). To the filtrate is added in one portion with stirring 8.21 g. (0.05 mole) of p-nitrophenylisocyanate as a solution in benzene (the isocyanate solution is filtered prior to use). After stirring one hour, the solid, 1-(1-methyl-2-pyrrolidylidene)-3-p-nitrophenylurea, is collected and dried, m.p. = 180°-182° C. Recrystallization from acetone-methanol gives pure product, m.p. = 182°-183° C.

Workup

  1. additionTo a suspension of 6.73 g
  2. customthe benzene layer is decanted onto excess anhydrous potassium carbonate
  3. filtrationThe combined extracts are filtered rapidly
  4. dry with materialfrom drying agent (dicalite pad and suction)
  5. additionTo the filtrate is added in one portion
  6. stirringwith stirring 8.21 g
  7. stirringAfter stirring one hour
  8. customthe solid, 1-(1-methyl-2-pyrrolidylidene)-3-p-nitrophenylurea, is collected
  9. customdried
  10. customRecrystallization from acetone-methanol
  11. customgives pure product, m.p. = 182°-183° C.

Sources & evidence

ORD record
ord-deed00d637dc4166b38f8ea4a7994f7f
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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