Ammonia → 4-Vinylbenzylamine

HRID 1107593Notes

Reaction equation

HRID 1107593 reaction equation
[CH:1]([CH:3](Cl)[C:4]1[CH:9]=CC=[CH:6][CH:5]=1)=C.[NH3:11].[Cl-].[NH4+].[CH:14](O)([CH3:16])[CH3:15]>>[NH2:11][CH2:15][C:14]1[CH:16]=[CH:9][C:4]([CH:3]=[CH2:1])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 110734664-Vinylbenzylamine

Procedure

To a 250 mL flask was added vinylbenzyl chloride (7.63 g, 0.050 mol), concentrated aqueous ammonia (9.8 mL), and isopropanol (40 mL). The mixture was stirred for one week, at which point a large quantity of crystalline material (ammonium chloride) had precipitated. The solid was filtered off and washed with isopropanol. The mother liquor was evaporated on a rotary evaporator until no ammonia odor could be detected. Isopropanol (50 mL) was then added, and the mixture refrigerated for several hours. Following refrigeration, ammonium chloride which had precipitated was filtered off to yield 4-aminomethylstyrene which was used without further purification.

Workup

  1. customhad precipitated
  2. filtrationThe solid was filtered off
  3. washwashed with isopropanol
  4. customThe mother liquor was evaporated on a rotary evaporator until no ammonia odor
  5. additionIsopropanol (50 mL) was then added
  6. waitthe mixture refrigerated for several hours
  7. customhad precipitated
  8. filtrationwas filtered off

Sources & evidence

ORD record
ord-f717c95d36a343d3ac75b5259614404f
Source dataset
uspto-grants-2000_05
Patent number
US06060517

Reaction notes

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