Methanol → HCID 86735190, compound

HRID 1439124Notes

Reaction equation

HRID 1439124 reaction equation
[CH3:1]O.C(N(CC)CC)C.[C:10]1([N:16](CCl)[C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:24](OCC)(=[O:26])C>>[C:10]1([N:16]([O:26][CH3:24])[C:17](=[O:21])[N:18]([CH3:20])[CH2:19][CH3:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21398151HCID 21398151, compound

Product 1

HCID 86735190HCID 86735190, compound

Procedure

A solution of 3.3 g (0.1 mole) of methanol and 10.1 g (0.1 mole) of triethylamine were added dropwise to a solution of 23 g (0.1 mole) of 3-phenyl-3-chloromethyl-1,1-dimethylurea in 125 ml of ethyl acetate, while stirring and cooling externally, is such a way that the reaction temperature did not exceed 20° C. After stirring for one hour at room temperature, the precipitate so produced was filtered off and well washed with about 50 ml of ethyl acetate. The combined filtrates and wash solutions were freed of the solvent in vacuo and the resulting oil was taken up in 100 ml of benzene and twice washed with 50 ml of water at a time. The organic phase was dried over sodium sulfate and the solvent was distilled off. The oily residue was taken up in 100 ml of benzene and twice washed with 50 ml of water at a time. The organic phase was dried over sodium sulfate and the solvent was distilled off. The oily residue was taken up in 100 ml of a 1:1 mixture of ether and petroleum ether, the solution was filtered and the solvent of the filtrate was distilled off in vacuo. 17.5 g (84% of theory) of 3-phenyl-3-methoxy-methyl-1,1-dimethylurea were left as an oil.

Workup

  1. temperaturecooling externally
  2. customdid not exceed 20° C
  3. stirringAfter stirring for one hour at room temperature
  4. customthe precipitate so produced
  5. filtrationwas filtered off
  6. washwell washed with about 50 ml of ethyl acetate
  7. washThe combined filtrates and wash solutions
  8. washtwice washed with 50 ml of water at a time
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. distillationthe solvent was distilled off
  11. washtwice washed with 50 ml of water at a time
  12. dry with materialThe organic phase was dried over sodium sulfate
  13. distillationthe solvent was distilled off
  14. additionThe oily residue was taken up in 100 ml of a 1:1 mixture of ether and petroleum ether
  15. filtrationthe solution was filtered
  16. distillationthe solvent of the filtrate was distilled off in vacuo
  17. wait17.5 g (84% of theory) of 3-phenyl-3-methoxy-methyl-1,1-dimethylurea were left as an oil

Sources & evidence

ORD record
ord-7a0109c951af4cb38cfaeb1098238b29
Source dataset
uspto-grants-1977_11
Patent number
US04058392

Reaction notes

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