Pyridine → HCID 21569058, compound

HRID 1579707Notes

Reaction equation

HRID 1579707 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[CH3:6][N:7]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[N:8]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].N1C=CC=CC=1>C1C=CC=CC=1>[CH3:6][N:7]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[N:8]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](=[O:25])[NH:5][C:3]([NH:2][CH3:1])=[O:4])=[CH:22][CH:21]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11719MethylureaHCID 215690594-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride

Product 1

HCID 21569058HCID 21569058, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7.4 g. of methyl urea, 46.7 g. of 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride, 8 g. of pyridine and 200 ml. of benzene were mixed and refluxed for 8 hours. After cooling down, the mixture was poured onto water and extracted with an ether/methylene chloride mixture. The extract was washed with water, with 1 N hydrochloric acid and again with water, dried over sodium sulfate and freed of the solvent by distillation. The residue crystallized upon triturating with methanol. The crystals were filtered off and dried, yielding 1-methyl-2-[4-(4-methyl-allophanoyl)-benzyl]-1,2-dicarbobenzoxy-hydrazine melting at 141°-142°. 25 g. thereof were dissolved in 50 ml. of glacial acetic acid and to it were added 100 ml. of a 33% solution of hydrobromic acid in glacial acetic acid. After 4 hours standing, the crystals formed were filtered off, washed with glacial acetic acid and ether, and recrystallized from methanol, yielding 1-methyl-2-[4-(4-methyl-allphanoyl)benzyl]-hydrazine hydrobromide of melting point 183°-183.5°.

Workup

  1. temperaturerefluxed for 8 hours
  2. temperatureAfter cooling down
  3. additionthe mixture was poured onto water
  4. extractionextracted with an ether/methylene chloride mixture
  5. washThe extract was washed with water, with 1 N hydrochloric acid and again with water
  6. dry with materialdried over sodium sulfate
  7. distillationfreed of the solvent by distillation
  8. customThe residue crystallized
  9. customupon triturating with methanol
  10. filtrationThe crystals were filtered off
  11. customdried

Sources & evidence

ORD record
ord-7d284273e37c4e1d9e2fbf5a56c9593a
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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