Ethyl chloroformate → HCID 20474131, compound

HRID 2295831Notes

Reaction equation

HRID 2295831 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[CH2:9][NH:8]2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](Cl)=[O:21])[CH3:18]>>[CH2:17]([O:19][C:20]([N:8]1[CH2:9][C:10](=[O:14])[NH:11][C:12](=[O:13])[N:7]1[CH2:6][C:5]1[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:21])[CH3:18]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 20474130HCID 20474130, compound

Product 1

HCID 20474131HCID 20474131, compoundYield 50%

Procedure

Into a 50 ml round bottomed flask equipped with an efficient condenser sealed with a calcium chloride tube were placed 10 ml of ethylchloroformate and 1 g of 2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine-3,5-dione. The mixture was refluxed for 3 hours, the solvent was removed in vacuum and ice water was added cautiously to the residue. The solution was adjusted to a neutral pH with a saturated solution of sodium bicarbonate. The crystals thus formed were filtered off by suction and recrystallized from isopropanol to yield 0.8 g (50%) of 1-ethoxycarbonyl-2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine-3,5-dione; m.p. 135°.

Workup

  1. customInto a 50 ml round bottomed flask equipped with an efficient condenser
  2. customsealed with a calcium chloride tube
  3. temperatureThe mixture was refluxed for 3 hours
  4. customthe solvent was removed in vacuum and ice water
  5. additionwas added cautiously to the residue
  6. customThe crystals thus formed
  7. filtrationwere filtered off by suction
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-0e943fdfbd21495796eb023317cdcf29
Source dataset
uspto-grants-1984_01
Patent number
US04426522

Reaction notes

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