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

HRID 1973953Notes

Reaction equation

HRID 1973953 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 K 2 CO 3 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 K 2 CO 3
  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-7ede211cffd24e78ab2f05f4f115663e
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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