Urea → HCID 21424819, compound

HRID 258829Notes

Reaction equation

HRID 258829 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][OH:12].N[C:14](N)=[O:15].[OH-].[Na+]>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][CH2:11][OH:12])[C:14](=[O:15])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 3

HCID 1176UreaHCID 14798Sodium HydroxideHCID 2849642-[(2-amino-4-chlorophenyl)amino]ethanol

Product 1

HCID 21424819HCID 21424819, compound

Procedure

A mixture of 9 parts of 2-[(2-amino-4-chlorophenyl)amino]-ethanol and 9 parts of urea is stirred and heated for 2 hours at 180°-190° C. After cooling the reaction mixture is treated with concentrated sodium hydroxide solution. The obtained solution is filtered from some unsoluble matter. It is then treated with activated charcoal and filtered again. The filtrate is acidified with concentrated hydrochloric acid. After keeping overnight at room temperature, the precipitated solid is filtered off, washed and dried, to yield 5 parts of 5-chloro-1-(2-hydroxyethyl)-1,3-dihydro-2H-benzimidazol-2-one; mp. 176°-178.2° C; pale-brown, amorphous powder.

Workup

  1. temperatureheated for 2 hours at 180°-190° C
  2. temperatureAfter cooling the reaction mixture
  3. filtrationThe obtained solution is filtered from some unsoluble matter
  4. additionIt is then treated with activated charcoal
  5. filtrationfiltered again
  6. filtrationthe precipitated solid is filtered off
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-6f9f37ac6930466785050fb0862e9442
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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