Benzene, 1-isocyanato-4-nitro- → 1-(1-Methyl-2-piperidylidene)-3-(4-nitrophenyl)urea

HRID 2071525Notes

Reaction equation

HRID 2071525 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1)([O-:11])=[O:10]>C1C=CC=CC=1>[CH3:8][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[N:1][C:19]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:17][CH:16]=1)=[O:20]

Participants

4

Reactant 2

HCID 66012Benzene, 1-isocyanato-4-nitro-HCID 124490281-Methylpiperidin-2-imine

Product 1

HCID 544628451-(1-Methyl-2-piperidylidene)-3-(4-nitrophenyl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The hydrochloride salt of 2-imino-1-methylpiperidine (7.43 g.; 0.05 mole) is converted to the free base in benzene in the usual manner. After drying over K2CO3 and filtering, a benzene solution of 0.05 mole of p-nitrophenylisocyanate is added dropwise with stirring. After addition is complete, further stirring is continued for about 6 hours at room temperature. The benzene is evaporated in vacuo and the solid residue is recrystallized from methanol to give the product, 1-(1-methyl-2-piperidylidene)-3-(4-nitrophenyl)urea:

Workup

  1. dry with materialAfter drying over K2CO3
  2. filtrationfiltering
  3. additionAfter addition
  4. stirringfurther stirring
  5. customThe benzene is evaporated in vacuo
  6. customthe solid residue is recrystallized from methanol

Sources & evidence

ORD record
ord-fe59d770e6b1461699b5cf08b39b8011
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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