Urea → HCID 13792185, compound

HRID 1729791Notes

Reaction equation

HRID 1729791 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.N[C:25](N)=[O:26]>>[O:26]=[C:25]1[N:12]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[NH:1]1

Participants

3

Reactant 2

HCID 1176UreaHCID 13792171HCID 13792171, compound

Product 1

HCID 13792185HCID 13792185, compound

Conditions

Temperature
100 °C

Procedure

56.27 parts of ethyl 4-[2-amino-4-(trifluoromethyl)-phenylamino]-1-piperidinecarboxylate and 15.6 parts of urea are mixed thoroughly in a mortar. The mixture is stirred and heated on an oil-bath at 170°-180° C for 3 hours. The reaction mixture is cooled to 100° C and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding ethyl 4-[1,3-dihydro-2-oxo-5-(trifluoromethyl)-2H-benzimidazol-1-yl]-1-piperidinecarboxylate.

Workup

  1. temperatureheated on an oil-bath at 170°-180° C for 3 hours
  2. extractionthe product is extracted with methylbenzene
  3. washThe extract is washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-39b894d058cc47bba52f7bdaff21beb1
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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