Water → HCID 19809155, compound

HRID 373975Notes

Reaction equation

HRID 373975 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=1.[C:13]1([O:19][CH2:20][CH:21]2[O:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O>[OH:23][CH:21]([CH2:20][O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:22][NH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]([NH2:12])=[O:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31217Phenyl glycidyl etherHCID 198091145-(3-Aminopropyl)thiophene-2-carboxamide

Product 1

HCID 19809155HCID 19809155, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

921 mg of 5(3-aminopropyl)-2-thiophenecarboxamide and 0.68 ml of 2,3-epoxypropyl phenyl ether were heated to 90° in 15 ml of dimethylsulfoxide for 14 hours. The reaction mixture was poured into water and extracted with methylene chloride. The dried methylene chloride solutions were evaporated in vacuo and the residue was chromatographed on silica gel, whereby there were obtained 800 mg of 5-[3-[[(RS)-2-hydroxy-3-phenoxypropyl]amino]propyl]-2-thiophenecarboxamide, m.p. 129°-130°, ε276 =12130.

Workup

  1. extractionextracted with methylene chloride
  2. customThe dried methylene chloride solutions were evaporated in vacuo
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0fdb90df6da140f3b8ebe9c5135e6436
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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