Hydrochloric Acid → HCID 19760912, compound

HRID 892690Notes

Reaction equation

HRID 892690 reaction equation
[CH3:1][C:2]([C:4]1[O:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)=[O:3].Cl.[CH3:17][NH:18][CH3:19].[CH2:20]=O.Cl>C(O)(C)C.C(O)CCC>[ClH:15].[CH3:17][N:18]([CH3:20])[CH2:19][CH2:1][C:2]([C:4]1[O:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 15035464HCID 15035464, compound

Product 1

HCID 19760912HCID 19760912, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 22 g. (0.10 mole) of 5-(p-chlorophenyl)-2-furyl methyl ketone, 16 g. (0.20 mole) of dimethylamine hydrochloride, 6 g (0.20 mole) of paraformaldehyde, 100 ml. of n-butanol, and I ml. of concentrated HCl is heated under reflux for 2 hr. Solvent is removed on a rotary evaporator and the yellow, residual solid is partitioned between ether and water. The layers are separated and the water layer is washed with ether. The water layer is made basic with 1N NaOH solution and is extracted twice with ether. The ethereal layers are dried over MgSO4 and are concentrated on a rotary evaporator to give a residual semi-solid. The solid is dissolved in 350 ml. of isopropanol and is treated with ethereal HCl. The solid which is deposited is collected by filtration and is dried in a 60° oven to give 13 g (42%) of product.

Workup

  1. temperatureunder reflux for 2 hr
  2. customSolvent is removed on a rotary evaporator
  3. customthe yellow, residual solid is partitioned between ether and water
  4. customThe layers are separated
  5. washthe water layer is washed with ether
  6. extractionis extracted twice with ether
  7. dry with materialThe ethereal layers are dried over MgSO4
  8. concentrationare concentrated on a rotary evaporator
  9. customto give a residual semi-solid
  10. dissolutionThe solid is dissolved in 350 ml
  11. filtrationThe solid which is deposited is collected by filtration
  12. customis dried in a 60° oven

Sources & evidence

ORD record
ord-cb1f964481924853b3907f0e39d16610
Source dataset
uspto-grants-1992_06
Patent number
US05118708

Reaction notes

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