Phosgene → HCID 20314248, compound

HRID 2419687Notes

Reaction equation

HRID 2419687 reaction equation
C(N(CC)CC)C.[C:8]([Cl:11])(Cl)=[O:9].[S:12]([N:16]1[CH2:20][CH2:19][NH:18][C:17]1=[O:21])(=[O:15])(=[O:14])[NH2:13]>ClCCl>[Cl:11][C:8]([N:18]1[CH2:19][CH2:20][N:16]([S:12](=[O:15])(=[O:14])[NH2:13])[C:17]1=[O:21])=[O:9]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 20314215HCID 20314215, compound

Product 1

HCID 20314248HCID 20314248, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 17.8 parts by vol. of triethylamine in 30 parts by vol. of dichloromethane was added dropwise over the course of 2 hrs. to a mixture of 100 parts by vol. of dichloromethane, 6.15 parts by vol. of (condensed) phosgene and 7.0 parts by wt. of 1-sulphamyl-2-oxo-imidazolidine at 20° C and the mixture was then left to stand for 17 hrs. The precipitate present was removed by filtration, the filtrate was concentrated by evaporation in vacuo and the residue was repeatedly extracted with ethyl acetate at 20° C. The ethyl acetate extracts were combined. On evaporation, they left a hard varnish. The IR spectrum showed a strong acid chloride band at 1,805 cm-1 (Nujol). Furthermore, it could be seen from the IR spectrum that the substance still contained considerable amounts of the starting product.

Workup

  1. waitthe mixture was then left
  2. customThe precipitate present was removed by filtration
  3. concentrationthe filtrate was concentrated by evaporation in vacuo
  4. extractionthe residue was repeatedly extracted with ethyl acetate at 20° C
  5. customOn evaporation, they
  6. waitleft a hard varnish

Sources & evidence

ORD record
ord-80233f227a254a1eb64917cf8cc2f1fe
Source dataset
uspto-grants-1978_08
Patent number
US04107304

Reaction notes

Loading…