Urea → HCID 21500249, compound

HRID 1729808Notes

Reaction equation

HRID 1729808 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH3:20])[CH2:11]1.N[C:22](N)=[O:23]>CC1C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH3:20])[CH2:11]3)[C:22](=[O:23])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 21500251HCID 21500251, compound

Product 1

HCID 21500249HCID 21500249, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 36 parts of methyl 4-(2-amino-4-chlorophenylamino)-2-methyl-1-piperidinecarboxylate and 14 parts of urea is stirred and heated in an oil-bath at 160° C. for 4 hours. After cooling, the reaction mixture is disslved in methylbenzene. The solution is washed successively three times with water, twice with a diluted hydrochloric acid solution and again three times with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silicagel, using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding methyl 4-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-2-methyl-1-piperidinecarboxylate as an oily residue.

Workup

  1. temperatureAfter cooling
  2. washThe solution is washed successively three times with water
  3. dry with materialtwice with a diluted hydrochloric acid solution and again three times with water, dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe oily residue is purified by column-chromatography over silicagel
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Sources & evidence

ORD record
ord-864f4c2a6ee04fec9a415680487f5bfb
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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