Hydrochloric Acid → HCID 10198071, compound

HRID 345623Notes

Reaction equation

HRID 345623 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C(O[CH:11](OCC)[CH2:12][NH2:13])C.[BH4-].[Na+].[C:19]([S-:21])#[N:20].[K+].Cl>C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:13]1[CH:12]=[CH:11][NH:20][C:19]1=[S:21]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 73642-ThiophenecarboxaldehydeHCID 695242,2-DiethoxyethylamineHCID 516872Potassium thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 10198071HCID 10198071, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture of 33.6 g (0.3 mol) thiophene-2-carboxaldehyde, 39.9 g (0.3 mol) aminoacetaldehyde diethyl acetal, 0.3 g of 4-toluenesulfonic acid (TsOH) and 200 ml ethanol is placed in a 500 ml flask and heated to reflux. After 2 hours, the reaction is concentrated and the residue dissolved in 250 ml ethanol. Solid NaBH4 (12.5 g, 0.33 mol) is added in small portions. The reaction is refluxed for 11/2 hours, cooled to room temperature and poured into cold water. The product is extracted into CH2Cl2 (2×250 ml). After drying (Na2SO4) and concentration, 66.7 g crude product is obtained as a pale yellow oil. 22.9 g (0.1 mol) of the crude amine is placed in a 500 ml flask along with 11.7 g (0.12 mol) KSCN, 150 ml ethanol, 40 ml water and 15 ml concentrated hydrochloric acid. After refluxing for 5 hours, the reaction is poured onto 1 liter of ice water. The white crystals are collected and dried to give 12.0 g (61%) product, mp 128°-130° C. (EtOH).

Workup

  1. customis placed in a 500 ml flask
  2. temperatureheated to reflux
  3. concentrationthe reaction is concentrated
  4. dissolutionthe residue dissolved in 250 ml ethanol
  5. temperatureThe reaction is refluxed for 11/2 hours
  6. extractionThe product is extracted into CH2Cl2 (2×250 ml)
  7. customAfter drying
  8. concentration(Na2SO4) and concentration
  9. custom66.7 g crude product is obtained as a pale yellow oil
  10. temperatureAfter refluxing for 5 hours
  11. customThe white crystals are collected
  12. customdried

Sources & evidence

ORD record
ord-b199751ad5d04468ae5c32ebe4bb8f5b
Source dataset
uspto-grants-1991_10
Patent number
US05057613

Reaction notes

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