HCID 14390500, compound → HCID 14676655, compound

HRID 2351640Notes

Reaction equation

HRID 2351640 reaction equation
[NH2:1][C:2](=[O:21])[CH2:3][NH:4][C:5]1[C:10]([NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:9][CH:8]=[CH:7][N:6]=1>C(O)CO>[Cl:19][C:15]1[CH:14]=[C:13]([C:12]2[N:4]([CH2:3][C:2]([NH2:1])=[O:21])[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:10]3[N:11]=2)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 14390500HCID 14390500, compound

Product 1

HCID 14676655HCID 14676655, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
190 °C

Procedure

A suspension of N-[2-[(2-amino-2-oxoethyl)amino]-3-pyridinyl]-3-chlorobenzamide (8.7 g, 0.029 mole) in 200 ml of ethylene glycol was heated at 190° C. for 40 minutes. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was diluted with water to produce a white precipitate. The mixture was refrigerated and the precipitate was filtered, washed with water, and dried under high vacuum at room temperature overnight, then at 60° C. for 6 hrs. The sample was recrystallized from methanol-water (~40/60) and refrigerated. The crystalline precipitate was filtered, washed with water, and dried under high vacuum at room temperature overnight. The sample was redried under high vacuum at 60° C. overnight to give 5.48 g (66%) of title compound, mp. 245°-47° C.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was diluted with water
  4. customto produce a white precipitate
  5. filtrationthe precipitate was filtered
  6. washwashed with water
  7. customdried under high vacuum at room temperature overnight
  8. customThe sample was recrystallized from methanol-water (~40/60)
  9. filtrationThe crystalline precipitate was filtered
  10. washwashed with water
  11. customdried under high vacuum at room temperature overnight
  12. customThe sample was redried under high vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-297e33ceeea24dfcb10c562b911c3e2d
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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