Tetrahydrofuran → HCID 20426458, compound

HRID 615584Notes

Reaction equation

HRID 615584 reaction equation
[O:1]1[CH2:5]CCC1.ClC(OC(Cl)(Cl)Cl)=O.[CH2:14]([O:16][C:17]([CH2:19][NH:20][CH2:21][C:22]1[O:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH3:15].[NH:27]1[CH:31]=[CH:30][N:29]=[N:28]1>O>[CH2:14]([O:16][C:17]([CH2:19][N:20]([CH2:21][C:22]1[O:26][CH:25]=[CH:24][CH:23]=1)[C:5]([N:27]1[CH:31]=[CH:30][N:29]=[N:28]1)=[O:1])=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 10426DiphosgeneHCID 13365154Ethyl 2-{[(furan-2-yl)methyl]amino}acetateHCID 178418936HCID 178418936, compound

Product 1

HCID 20426458HCID 20426458, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a solution of 100 ml of dry tetrahydrofuran containing 10 g (0.05 mol) of trichloromethyl chloroformate, 30 ml of a dry tetrahydrofuran solution containing 13 g (0.071 mol) of N-(1-ethoxycarbonylmethyl)-N-furfurylamine was added dropwise while cooling the former at 0° to 5° C. After stirring the mixture for 30 min at room temperature, 200 ml of dry tetrahydrofuran solution containing 9.8 g (0.121 mol) of triazole was added at 10° to 15° C. to the mixture. Then the mixture was gradually heated to boiling and reacted for about one hour while refluxing. After the reaction was over, the reaction mixture was cooled to a room temperature and poured into water. The mixture was extracted with ethyl acetate, and the extract was treated by the usual procedures of washing with water, separating, dehydrating and concentrating. The thus obtained concentrate was subjected to silica gel chromatography to obtain 13 g (0.0468 mol) of an oily substance. The thus obtained Compound No. 4 gave the following physical constants:

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling the former at 0° to 5° C
  3. additionwas added at 10° to 15° C. to the mixture
  4. temperatureThen the mixture was gradually heated
  5. customreacted for about one hour
  6. temperaturewhile refluxing
  7. temperaturewas cooled to a room temperature
  8. extractionThe mixture was extracted with ethyl acetate
  9. additionthe extract was treated by the usual procedures
  10. washof washing with water
  11. customseparating
  12. concentrationconcentrating
  13. customThe thus obtained
  14. concentrationconcentrate
  15. customto obtain 13 g (0.0468 mol) of an oily substance
  16. custom4 gave the following physical constants

Sources & evidence

ORD record
ord-96ba29286f674b2589b4a9fdae22ce67
Source dataset
uspto-grants-1985_02
Patent number
US04500536

Reaction notes

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