1,1-Dichloroethane → 1-[Tris(2-fluoro-2,2-dinitroethoxy)methyl]imidazolidin-2-one

HRID 615514Notes

Reaction equation

HRID 615514 reaction equation
ClC(SS[C:7]([O:28][CH2:29][C:30]([F:37])([N+:34]([O-:36])=[O:35])[N+:31]([O-:33])=[O:32])([O:18][CH2:19][C:20]([N+:25]([O-:27])=[O:26])([N+:22]([O-:24])=[O:23])[F:21])[O:8][CH2:9][C:10]([N+:15]([O-:17])=[O:16])([N+:12]([O-:14])=[O:13])[F:11])(Cl)Cl.ClCl.[NH:40]1[CH2:44][CH2:43][NH:42][C:41]1=[O:45].ClC(Cl)C.[K+].[Br-]>ClCCCl.O.C(Cl)(Cl)Cl>[F:11][C:10]([N+:15]([O-:17])=[O:16])([N+:12]([O-:14])=[O:13])[CH2:9][O:8][C:7]([O:28][CH2:29][C:30]([N+:34]([O-:36])=[O:35])([N+:31]([O-:33])=[O:32])[F:37])([O:18][CH2:19][C:20]([N+:25]([O-:27])=[O:26])([N+:22]([O-:24])=[O:23])[F:21])[N:40]1[CH2:44][CH2:43][NH:42][C:41]1=[O:45]

Participants

9

Reactant 5

HCID 63651,1-DichloroethaneHCID 84532-ImidazolidinoneHCID 24526ChlorineHCID 253877Potassium BromideHCID 131492082-{Bis(2-fluoro-2,2-dinitroethoxy)[(trichloromethyl)disulfanyl]methoxy}-1-fluoro-1,1-dinitroethane

Product 1

HCID 204288391-[Tris(2-fluoro-2,2-dinitroethoxy)methyl]imidazolidin-2-one

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 19.6 g (0.03 mol) of tris(2-fluoro-2,2-dinitroethoxy)methyl trichloromethyl disulfide in 55 ml of dry 1,2-dichloroethane at 55°-60° C. was treated with chlorine gas for 2 hours, then held at 55°-60° C. for 2 hours before the solvent was removed with a stream of nitrogen. The residue was washed three times with hexane to give a white solid which was dissolved in 60 ml of dry 1,2-dichloroethane. 2-Imidazolidone (6.0 g, 0.069 mol) was added and the mixture was stirred at ambient temperature for 24 hours before the insoluble solid was removed by filtration and stirred with water to give 11.63 g, mp 154°-156° C. Removal of the solvent from the dichloroethane mother liquor (reaction solution) gave a residue which was stirred with chloroform and water to yield an additional 1.12 g, mp 152°-155° C. [total yield=12.75 g (76%)]. The analytical sample from dichloroethane had mp 155°-156° C.; H--NMR(C6D6): δ 4.46 (d, 6H); 4.00 (s, 1H), 2.66 (t, 2H), 2.20 (t, 2H); IR (KBr): 3480 (NH), 1725 (C=O), 1605 (NO2) cm-1.

Workup

  1. customwas removed with a stream of nitrogen
  2. washThe residue was washed three times with hexane
  3. customto give a white solid which
  4. customwas removed by filtration
  5. stirringstirred with water
  6. customto give 11.63 g, mp 154°-156° C
  7. customRemoval of the solvent
  8. customfrom the dichloroethane mother liquor (reaction solution)
  9. customgave a residue which
  10. customto yield an additional 1.12 g, mp 152°-155° C. [total yield=12.75 g (76%)]

Sources & evidence

ORD record
ord-9bca4d1b088c4a7b83cfdaa0cd724fb8
Source dataset
uspto-grants-1985_02
Patent number
US04499309

Reaction notes

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