HCID 14390496, compound → Ahr 12245

HRID 621886Notes

Reaction equation

HRID 621886 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][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=[CH:7][N:6]=1>C(O)CO.CO>[Cl:19][C:16]1[CH:17]=[CH:18][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:14][CH:15]=1

Participants

4

Reactant 1

HCID 14390496HCID 14390496, compound

Product 1

HCID 3082931Ahr 12245Yield 25%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of N[2-[(2-amino-2-oxoethyl)amino]-3-pyridinyl]-4-chlorobenzamide (6.0 g, 0.02 mole) in 150 ml of ethylene glycol was heated at 190° C. for 40 minutes. The precipitate, which formed, was filtered off and washed with water. The filtrate was diluted with water to produce a second crop. The first crop was heated to boiling in 300 ml of methanol, filtered through a Celite pad, seeded, and refrigerated overnight. The crystalline precipitate was filtered, washed with cold methanol, and dried under high vacuum at 60° C. overnight to give 1.42 g (25%) of title compound, mp 270°-1° C.

Workup

  1. customThe precipitate, which formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. additionThe filtrate was diluted with water
  5. customto produce a second crop
  6. temperatureThe first crop was heated
  7. filtrationfiltered through a Celite pad
  8. customrefrigerated overnight
  9. filtrationThe crystalline precipitate was filtered
  10. washwashed with cold methanol
  11. customdried under high vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-317c61a3a78b4b5e8d65237afc8c6051
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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