Hydrochloric Acid → HCID 54515577, compound

HRID 1702692Notes

Reaction equation

HRID 1702692 reaction equation
[CH2:1]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([CH2:22][CH2:23][C:24]#N)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.CC[O:31]CC>>[CH2:1]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([CH:22]=[CH:23][CH:24]=[O:31])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 20525824HCID 20525824, compound

Product 1

HCID 54515577HCID 54515577, compound

Procedure

A solution of 10.0 g. of 4-hexadecylaminohydrocinnamonitrile in 100 ml. of dry ether is added rapidly to a mixture of 10.2 g. of anhydrous stannous chloride and 80 ml. of ether which has been saturated with dry hydrogen chloride for 2 hours. Dry hydrogen chloride is again bubbled through the reaction mixture which is stirred for 1 hour and allowed to stand for 20 hours. The ethereal solution is decanted from the semi-solid product which is washed again with ether and then treated with water and heated to reflux for 3 hours. Cooling and extraction of the reaction mixture with ether provides 4-(hexadecylamino)cinnamaldehyde.

Workup

  1. customDry hydrogen chloride is again bubbled through the reaction mixture which
  2. waitto stand for 20 hours
  3. customThe ethereal solution is decanted from the semi-solid product which
  4. washis washed again with ether
  5. additiontreated with water
  6. temperatureheated
  7. temperatureto reflux for 3 hours
  8. temperatureCooling
  9. extractionextraction of the reaction mixture with ether

Sources & evidence

ORD record
ord-7395b06d7e5f493782bf82bd981a28f0
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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