Hydrochloric Acid → HCID 21390545, compound

HRID 462101Notes

Reaction equation

HRID 462101 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C=O.Cl.O.[Cl:20][CH:21](Cl)C(Cl)Cl>>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])[C:5]([CH2:21][Cl:20])=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 65911,1,2,2-TetrachloroethaneHCID 21390574HCID 21390574, compound

Product 1

HCID 21390545HCID 21390545, compound

Procedure

4.1 g of rac. 1-(3,4-dimethylphenyl)-2-acetamidopropane was dissolved in 40 ml of 1,1,2,2-tetrachlorethane in a 100-ml RB flask provided with a stirrer, thermometer, condenser, and gas inlet tube. Twelve ml of 37% formaldehyde was added, and a stream of hydrogen chloride passed into the stirred mixture as the temperature rose to 50°, where it was maintained for 5 hrs. At this point, the mixture remained overnight at room temperature. The reaction mixture was poured into water, the organic phase was washed twice with water, dried, and the solvent distilled in the rotary evaporator, leaving 4.2 g of a colorless oil. The oil was refluxed with four 100-ml-portions of petroleum ether (b.p. 60-0-°), and from the combined extracts, a mass of cottony needles separated. The solid was collected by filtration and freed of solvent in vacuo to yield the above-named product, m.p. 72°-73°.

Workup

  1. customprovided with a stirrer
  2. customrose to 50°
  3. temperaturewhere it was maintained for 5 hrs
  4. washthe organic phase was washed twice with water
  5. customdried
  6. distillationthe solvent distilled in the rotary evaporator

Sources & evidence

ORD record
ord-14ee64d27dc14e0295495dba62abf8cc
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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