Methanol → HCID 23321939, compound

HRID 280246Notes

Reaction equation

HRID 280246 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7](=O)[CH2:8][O:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=1[Cl:18])[CH3:2].CSC.B.CO>C1(C)C=CC=CC=1>[ClH:16].[Cl:16][C:15]1[CH:14]=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=1[O:9][CH2:8][CH2:7][NH:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 13653520HCID 13653520, compound

Product 1

HCID 23321939HCID 23321939, compoundYield 206.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 31.5 g (0.096 moles) N-(ethoxyethyl)-2.4.6-trichlorophenoxyacetamide in about 200 ml toluene, 18.2 ml (2 equivalents) borane methyl sulfide were added slowly. The resulting mixture was heated to about 60° C. and maintained at that temperature overnight. After cooling, methanol (about 100 ml) was slowly added to the system. After the addition was complete, the mixture was acidified by bubbling in HCl gas. Afterwards, the system was refluxed for about an hour. The solvent was removed by stripping. The residue was re-dissolved in methanol (about 100 ml) and the resulting mixture stripped well. The residue was well dried in vacuum to give 34.6 g of the product, a white solid, melting point 85°-87° C.

Workup

  1. additionwere added slowly
  2. temperaturemaintained at that temperature overnight
  3. temperatureAfter cooling
  4. additionAfter the addition
  5. customby bubbling in HCl gas
  6. temperatureAfterwards, the system was refluxed for about an hour
  7. customThe solvent was removed by stripping
  8. dissolutionThe residue was re-dissolved in methanol (about 100 ml)
  9. customThe residue was well dried in vacuum

Sources & evidence

ORD record
ord-5e177834f4214847b1c334fba597232b
Source dataset
uspto-grants-1986_05
Patent number
US04588735

Reaction notes

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