Triethylamine → HCID 18961050, compound

HRID 1708179Notes

Reaction equation

HRID 1708179 reaction equation
C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]1[S:27][C:26](=[O:28])[NH:25][CH:24]1[C:29]([OH:31])=O.[N+]([O-])(O)=O.[N+:36]([O:39][CH2:40][CH2:41][NH2:42])([O-:38])=[O:37]>O1CCCC1>[N+:36]([O:39][CH2:40][CH2:41][NH:42][C:29]([CH:24]1[CH:23]([C:19]2[O:18][CH:22]=[CH:21][CH:20]=2)[S:27][C:26](=[O:28])[NH:25]1)=[O:31])([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 18961048HCID 18961048, compound

Product 1

HCID 18961050HCID 18961050, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.58 ml of triethylamine and 0.47 ml of diethyl cyanophosphonate were added, whilst ice-cooling and stirring, to a suspension of 500 mg of 5-(furan-2-yl)2-oxothiazolidine-4-carboxylic acid and 476 mg of N-(2-nitrooxyethyl)amine nitrate in 50 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 3.5 hours, after which the solvent was removed by distillation under reduced pressure. The crystals which precipitated were triturated with diisopropyl ether and collected by filtration. These crystals were recrystallized from methylene chloride, to give 400 mg of the title compound as colorless crystals, melting at 117°-118° C.

Workup

  1. temperaturecooling
  2. customafter which the solvent was removed by distillation under reduced pressure
  3. customThe crystals which precipitated
  4. customwere triturated with diisopropyl ether
  5. filtrationcollected by filtration
  6. customThese crystals were recrystallized from methylene chloride

Sources & evidence

ORD record
ord-236124fd57764b04819cdf11e86cc0e9
Source dataset
uspto-grants-1994_10
Patent number
US05356918

Reaction notes

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