Potassium Hydroxide → HCID 15631972, compound

HRID 1194695Notes

Reaction equation

HRID 1194695 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2=[N:6][C:7]3[CH2:8][CH2:9][N:10]([CH3:15])[CH2:11][C:12]=3[C:13](Cl)=[C:4]2[CH:3]=1.Cl.[NH2:19][CH2:20][CH2:21][CH2:22][SH:23].[OH-].[K+]>C(O)C>[NH2:19][CH2:20][CH2:21][CH2:22][S:23][C:13]1[C:12]2[CH2:11][N:10]([CH3:15])[CH2:9][CH2:8][C:7]=2[N:6]=[C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 197870(3-Mercaptopropyl)ammonium chlorideHCID 12273863HCID 12273863, compound

Product 1

HCID 15631972HCID 15631972, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.0 g (0.0188 mol) of the compound of Example 6, 3.3 g (0.02244 m) of 3-aminopropanethiol hydrochloride, 15 ml of 18.5% aqueous potassium hydroxide (0.05 m) and 30 ml of absolute ethanol is refluxed for one and a half hours. After evaporation of the solution, the residue is dissolved in methylene chloride and extracted with water. Evaporation of the methylene chloride solution gives the free base. Recrystallization of the product from hexane affords the title compound as a crystaline solid (3.2 g, 53%), m.p. 87°-89° C.

Workup

  1. customAfter evaporation of the solution
  2. dissolutionthe residue is dissolved in methylene chloride
  3. extractionextracted with water
  4. customEvaporation of the methylene chloride solution
  5. customgives the free base
  6. customRecrystallization of the product from hexane

Sources & evidence

ORD record
ord-1773d2063a754b089878484c2958b53a
Source dataset
uspto-grants-1989_03
Patent number
US04816464

Reaction notes

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