Water → HCID 19809087, compound

HRID 373974Notes

Reaction equation

HRID 373974 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[S:8][C:7]([C:9]([NH2:11])=[O:10])=[CH:6][CH:5]=1.[C:12]1([O:18][CH2:19][CH:20]2[O:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:23]>CS(C)=O>[OH:22][CH:20]([CH2:19][O:18][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:21][N:1]([CH2:19][CH:20]([OH:22])[CH2:21][O:23][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][C:4]1[S:8][C:7]([C:9]([NH2:11])=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31217Phenyl glycidyl etherHCID 198091675-(2-Aminoethyl)thiophene-2-carboxamide

Product 1

HCID 19809087HCID 19809087, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.4 g of 5-(2-aminoethyl)-2-thiophenecarboxamide and 2.7 ml of 2,3-epoxypropyl phenyl ether were heated to 90° in 30 ml of dimethylsulfoxide for 18 hours. The reaction mixture was poured into water and extracted with methylene chloride. The dried methylene chloride solutions were evaporated and the residue was chromatographed on silica gel with ether-methanol. There were obtained 1.5 g of 5-[2-[bis-[(RS)-2-hydroxy-3-phenoxypropyl]amino]ethyl]-2-thiophenecarboxamide, ε277 =12580.

Workup

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

Sources & evidence

ORD record
ord-4db5f7baea7d44599ec1d3f1d4ac953a
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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