Methylamine → HCID 20293233, compound

HRID 2163833Notes

Reaction equation

HRID 2163833 reaction equation
[OH-].[Na+].[CH3:3][NH2:4].[CH:5]([CH:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:6]>>[CH:5]([CH:7]([N:4]([CH:7]([CH:5]=[CH2:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:6]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 20293233HCID 20293233, compound

Procedure

20 Grams (0.5 mole) of 98.2% sodium hydroxide pellets are dissolved, with stirring and cooling to a temperature maintained at 10° C., in a saturated solution of monomethylamine (large excess greater than 1 mole), which is prepared by bubbling gaseous monomethylamine into 200 ml. of distilled water at 10° C. until saturated. Then, 77.8 grams (0.5 mole) of 98% vinylbenzyl chloride are added at a uniform rate over a period of 30 minutes while maintaining the batch temperature below 20° C. Upon removing external cooling, the batch temperature rises to 32° C. in 1 hour as a result of an exotherm. The batch is then agitated at ambient temperature (26° C.) overnight. On stopping agitation, the phases cleanly separate within a period of 1 hour. The lower aqueous layer of 250 grams is withdrawn and discarded. The upper product layer of 50 grams is washed with three successive 100 ml. portions of water adjusted to a pH of 8.9, followed by one 100 ml. portion of distilled water (neutral pH). (Without the pH adjustment of the initial three wash portions, some foaming and emulsification occurs.) The washed product layer is then dried over calcium chloride and anhydrous sodium sulfate. Upon removing the drying agent, 38 grams of product is obtained. Analyses showed this material to have the following properties:

Workup

  1. temperaturecooling to a temperature
  2. customis prepared
  3. customby bubbling gaseous monomethylamine into 200 ml
  4. customat 10° C.
  5. temperaturewhile maintaining the batch temperature below 20° C
  6. customUpon removing external cooling
  7. customas a result of an exotherm
  8. stirringThe batch is then agitated at ambient temperature (26° C.) overnight
  9. customthe phases cleanly separate within a period of 1 hour
  10. customThe lower aqueous layer of 250 grams is withdrawn
  11. washThe upper product layer of 50 grams is washed with three successive 100 ml
  12. wash(Without the pH adjustment of the initial three wash portions
  13. dry with material) The washed product layer is then dried over calcium chloride and anhydrous sodium sulfate
  14. customUpon removing the drying agent

Sources & evidence

ORD record
ord-89f62f08c43f47628f1cfae9cb06bce6
Source dataset
uspto-grants-1979_01
Patent number
US04137264

Reaction notes

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