Tetrahydrofuran → Acetic acid, (((methylamino)carbonyl)amino)oxo-, butyl ester

HRID 247549Notes

Reaction equation

HRID 247549 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[O:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:12][NH:13][C:14]([NH2:16])=[O:15]>C(O)CCC>[CH3:8][CH2:9][CH2:10][CH2:11][O:7][C:2]([C:1]([NH:16][C:14]([NH:13][CH3:12])=[O:15])=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11719MethylureaHCID 65578Oxalyl chloride

Product 1

HCID 3064881Acetic acid, (((methylamino)carbonyl)amino)oxo-, butyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

8.5 ml of oxalyl chloride was added to 200 ml of tetrahydrofuran, 9.2 ml of butylalcohol was added dropwise for 30 minutes with stirring in an ice-water bath, and the solution was stirred for a hour in an ice-water bath. 7.4 g of methylurea was slowly added thereto and the solution was stirred for 15 hours at room temperature. After tetrahydrofuran was distilled off under the reduced pressure, water was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed three times with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The crude product was passed through a column of silica gel. Ethyl acetate was distilled off, and ether was added thereto. The precipitate was filtered off and recrystallized from ethyl acetate-hexane to give 11.2 g of 5-methyloxaluric acid butyl ester (compound 20).

Workup

  1. additionwas added dropwise for 30 minutes
  2. stirringthe solution was stirred for a hour in an ice-water bath
  3. stirringthe solution was stirred for 15 hours at room temperature
  4. distillationAfter tetrahydrofuran was distilled off under the reduced pressure, water
  5. additionwas added to the residue
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed three times with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationEthyl acetate was distilled off
  10. additionether was added
  11. filtrationThe precipitate was filtered off
  12. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d8d6d27a73294e0f86cc91158d2879ee
Source dataset
uspto-grants-1987_11
Patent number
US04708954

Reaction notes

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