Pyridine → HCID 21453097, compound

HRID 1283433Notes

Reaction equation

HRID 1283433 reaction equation
N1C=CC=CC=1.[S:7]([NH:11][C:12]([NH2:14])=[O:13])([CH3:10])(=[O:9])=[O:8].[C:15](Cl)([Cl:17])=[O:16]>ClCCl>[S:7]([NH:11][C:12]([NH:14][C:15]([Cl:17])=[O:16])=[O:13])([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 19365480Methanesulfonamide, N-(aminocarbonyl)-

Product 1

HCID 21453097HCID 21453097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 parts by volume of pyridine were added dropwise, while cooling, to a mixture of 10.5 parts by weight of N-mesylurea, 60 parts by volume of dichloromethane and 15.0 parts by weight of phosgene, while cooling, and after some hours at 0°C the excess of the phosgene was removed, the precipitate present was filtered off and the filtrate was completely concentrated in vacuo. A viscous oil remained, which had an absorption at 1800 cm-1 in the carbonyl region of the IR-spectrum. The substance was used without further purification for the production of the penicillin.

Workup

  1. temperaturewhile cooling
  2. customafter some hours at 0°C the excess of the phosgene was removed
  3. filtrationthe precipitate present was filtered off
  4. concentrationthe filtrate was completely concentrated in vacuo
  5. customan absorption at 1800 cm-1 in the carbonyl region of the IR-spectrum
  6. customThe substance was used without further purification for the production of the penicillin

Sources & evidence

ORD record
ord-ac15326028334b0fa9e14aab0ce4551f
Source dataset
uspto-grants-1976_08
Patent number
US03975375

Reaction notes

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