Phosgene → HCID 21453080, compound

HRID 1283024Notes

Reaction equation

HRID 1283024 reaction equation
[S:1]([N:11]=[C:12]1[NH:16][CH2:15][CH2:14][NH:13]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:17](Cl)([Cl:19])=[O:18].C(N(CC)CC)C>O1CCCC1>[Cl:19][C:17]([N:16]1[CH2:15][CH2:14][N:13]=[C:12]1[NH:11][S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3])=[O:18]

Participants

5

Reactant 3

HCID 6371Phosgene2×HCID 8471TriethylamineHCID 178427426HCID 178427426, compound

Product 1

HCID 21453080HCID 21453080, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

12 parts by weight of 2-tosylimino-imidazolidine (produced as described by Gompper and Hagele, Ber. 99, 2892 [1966]) were partly dissolved by 10 minutes' boiling in 150 parts by volume of absolute tetrahydrofurane, and thereafter rapidly cooled to 0°C by swirling in an ice bath. 6 parts by weight of phosgene were added to the suspension while stirring, the mixture was stirred for 30 minutes at 0°C, 5 parts by weight of triethylamine were then added dropwise and the whole was then stirred for a further 3 hours at room temperature. The excess phosgene was blown out by means of a stream of dry air and the precipitated triethylamine hydrochloride was removed from the tetrahydrofurane solution by filtration and was thoroughly eluted with absolute tetrahydrofurane. The combined solutions were evaporated to dryness in vacuo and the residual oil was caused to crystallize by trituration with methylene chloride and ether, filtered off and dried in vacuo.

Workup

  1. customby swirling in an ice bath
  2. stirringthe mixture was stirred for 30 minutes at 0°C
  3. stirringthe whole was then stirred for a further 3 hours at room temperature
  4. customthe precipitated triethylamine hydrochloride was removed from the tetrahydrofurane solution by filtration
  5. washwas thoroughly eluted with absolute tetrahydrofurane
  6. customThe combined solutions were evaporated to dryness in vacuo
  7. customto crystallize by trituration with methylene chloride and ether
  8. filtrationfiltered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a42de72382fa4b6e855ab3abc4feb636
Source dataset
uspto-grants-1976_08
Patent number
US03974141

Reaction notes

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