Thionyl Chloride → HCID 13195262, compound

HRID 1284103Notes

Reaction equation

HRID 1284103 reaction equation
Cl.[N:2]1[C:3]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:21])[C:18]([OH:20])=O)=[CH:13][CH:12]=2)=[CH:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.S(Cl)(Cl)=O.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH:30][C:18](=[O:20])[CH:17]([C:14]1[CH:13]=[CH:12][C:11]([C:3]2[N:2]=[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][N:5]3[CH:4]=2)=[CH:16][CH:15]=1)[CH3:21]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 6813903455843-87-3

Product 1

HCID 13195262HCID 13195262, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

6.2 g of 2-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]propionyl chloride, which is produced by treating 2-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]-propionic acid hydrochloride with thionyl chloride in chloroform, is added to a solution of 2.6 g of N,N-dimethylethylenediamine in 50 ml of pyridine. The mixture is allowed to stand at room temperature for 3 hours, and concentrated under reduced pressure. The residue is neutralized with aqueous sodium bicarbonate solution. The crystalline precipitate is washed with water and recrystallized from toluene to give 2.3 g of N-(2-dimethylamino-ethyl)-2-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]propionamide melting at 149°-150°C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe crystalline precipitate is washed with water
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-1b182c6a4fd742a5b993a6057bb2ec11
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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