Dichloromethane → HCID 12667596, compound

HRID 2398627Notes

Reaction equation

HRID 2398627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH2:7])=[O:6].C(Cl)Cl.F[B-](F)(F)F.[CH2:20]([O+](CC)CC)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](=[NH:7])[O:6][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 11430Potassium CarbonateHCID 1376713,4-DichlorobenzamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 12667596HCID 12667596, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dichlorobenzamide (139 g.; 0.73 mole) suspended in 600 ml. of methylene chloride is added to 150 g. (0.8 mole) of triethyloxonium fluoroborate in 100 ml. of methylene chloride cooled in an ice-bath to 0° C. over a period of 10-15 min. At the end of the addition, the mixture is allowed to stir at room temperature overnight. The mixture is again cooled in an ice-bath and 141 g. of 50% potassium carbonate in water is added over 30 min. The mixture is stirred for 15 min., the methylene chloride layer separated and the solids washed with methylene chloride. The combined organic layer and washings are dried over sodium sulfate and concentrated in vacuo to a yellow oil which is treated with hexane. A small amount of solids are filtered and the filtrate concentrated to give, after drying in vacuo, 140 g. of the desired imino ether, m.p. 62°-64° C.

Workup

  1. additionAt the end of the addition
  2. temperatureThe mixture is again cooled in an ice-bath
  3. stirringThe mixture is stirred for 15 min.
  4. customthe methylene chloride layer separated
  5. washthe solids washed with methylene chloride
  6. dry with materialThe combined organic layer and washings are dried over sodium sulfate
  7. concentrationconcentrated in vacuo to a yellow oil which
  8. additionis treated with hexane
  9. filtrationA small amount of solids are filtered
  10. concentrationthe filtrate concentrated
  11. customto give
  12. customafter drying in vacuo, 140 g

Sources & evidence

ORD record
ord-6e140ea8e7fb46c9b6f3273a0776e3c6
Source dataset
uspto-grants-1977_05
Patent number
US04025506

Reaction notes

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