Hydrochloric Acid → HCID 70446579, compound

HRID 464023Notes

Reaction equation

HRID 464023 reaction equation
[Cl:1][CH2:2][CH:3]=[CH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.Cl.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>>[ClH:1].[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:2][CH:3]=[CH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 54009761HCID 54009761, compound

Product 1

HCID 70446579HCID 70446579, compound

Procedure

To 250 ml of diethylamine at 0° C. add 30 g (0.14 mole) of 1chloro-4-(4-nitrophenyl)-2-butene over a 30 minute period. Stir for 16 hr at room temperature. Remove the solvent in vacuo. Extract the residue with 200 ml of 10% hydrochloric acid. Extract the resulting solution 2×100 ml ethyl acetate and discard. Adjust the pH of the water layer to about 12 with 10% sodium hydroxide. Extract 3×100 ml methylene chloride. Take the combined organic extracts and dry over Na2SO4. Remove the solvent in vacuo. Dissolve the residue in 100 ml ethanol, and add 1.5 equivalents of concentrated hydrochloric acid. Evaporate off the solvent, and crystallize the residue with acetone to provide the title compound.

Workup

  1. customRemove the solvent in vacuo
  2. extractionExtract the residue with 200 ml of 10% hydrochloric acid
  3. extractionExtract the resulting solution 2×100 ml ethyl acetate and discard
  4. extractionExtract 3×100 ml methylene chloride
  5. dry with materialdry over Na2SO4
  6. customRemove the solvent in vacuo
  7. dissolutionDissolve the residue in 100 ml ethanol
  8. customEvaporate off the solvent
  9. customcrystallize the residue with acetone

Sources & evidence

ORD record
ord-fcb1899bf8a3442ea324d9420cf93289
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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