Trimethyl phosphite → HCID 21281101, compound

HRID 414584Notes

Reaction equation

HRID 414584 reaction equation
[CH:1]1([CH2:7][N:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].[P:22]([O:27]C)([O:25][CH3:26])[O:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:10]1([CH2:9][N:8]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[P:22]([O:25][CH3:26])([O:23][CH3:24])=[O:27])[C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 8472Trimethyl phosphiteHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 54414975HCID 54414975, compound

Product 1

HCID 21281101HCID 21281101, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-5 °C

Procedure

The solution of N-(cyclohexylmethyl)phenylmethanimine in chloroform was diluted to 100 mL with fresh chloroform. This solution was stirred and cooled to -5° C. Ethyl chloroformate (11.0 mL, 0.12 mole) was added, and the mixture was stirred for ten minutes. Trimethyl phosphite (13.0 mL, 0.11 mole) was added, and the cold mixture was stirred for an additional ten minutes. The mixture was allowed to warm to room temperature and stir for 30 minutes. This mixture was poured slowly into an aqueous solution of potassium carbonate. The resultant mixture was extracted with chloroform. The extract was washed with an aqueous solution saturated with sodium chloride and then was dried over anhydrous magnesium sulfate. The dried solution was filtered, and the filtrate was evaporated under reduced pressure, leaving an oil. This oil was purified by column chromatography on silica gel to yield ethyl N-cyclohexylmethyl-N-[phenyl(dimethoxyphosphinyl)methyl]carbamate as an oil.

Workup

  1. stirringthe mixture was stirred for ten minutes
  2. stirringthe cold mixture was stirred for an additional ten minutes
  3. temperatureto warm to room temperature
  4. stirringstir for 30 minutes
  5. extractionThe resultant mixture was extracted with chloroform
  6. washThe extract was washed with an aqueous solution saturated with sodium chloride
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationThe dried solution was filtered
  9. customthe filtrate was evaporated under reduced pressure
  10. customleaving an oil
  11. customThis oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6089359337df406985f82a93eee5e1ec
Source dataset
uspto-grants-1988_12
Patent number
US04792567

Reaction notes

Loading…