Methanesulfonyl chloride → HCID 20474105, compound

HRID 2295832Notes

Reaction equation

HRID 2295832 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.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:17][S:18]([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:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20474130HCID 20474130, compound

Product 1

HCID 20474105HCID 20474105, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 50 ml round bottomed flask equipped with a calcium chloride drying tube and a magnetic stirrer were placed 5 ml of dry pyridine and 1 g of 2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine-3,5 dione. The mixture was then stirred and cooled in an ice bath, 0.5 g of methanesulfonyl chloride was added dropwise. After the product had been added the mixture was brought to ambient temperature and stirred for 5 hours. The solvent was then removed in vacuum and the residue was neutralized with dilute hydrochloric acid. The crystals obtained were filtered off and recrystallized from alcohol to yield 0.8 g of 1-methane sulfonyl-2-(4'-chlorobenzyl)-hexahydro-1,2,4-triazine-3,5-dione; m.p. 145°.

Workup

  1. customInto a 50 ml round bottomed flask equipped with a calcium chloride drying tube and a magnetic stirrer
  2. temperaturecooled in an ice bath
  3. additionAfter the product had been added the mixture
  4. customwas brought to ambient temperature
  5. stirringstirred for 5 hours
  6. customThe solvent was then removed in vacuum
  7. customThe crystals obtained
  8. filtrationwere filtered off
  9. customrecrystallized from alcohol

Sources & evidence

ORD record
ord-9d368e52383745688fd1b4517dc5ccd0
Source dataset
uspto-grants-1984_01
Patent number
US04426522

Reaction notes

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