1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 20228701, compound

HRID 1731363Notes

Reaction equation

HRID 1731363 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:13]=[CH:14][C:15]2[S:19][C:18](=[O:20])[NH:17][C:16]=2[CH:21]=1.[H-].[Na+].Cl.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][Cl:30])[CH3:26].C[O-].[Na+]>CN(C)C=O.CO>[ClH:30].[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:13]=[CH:14][C:15]2[S:19][C:18](=[O:20])[N:17]([CH2:26][CH2:25][N:27]([CH2:31][CH3:32])[CH2:28][CH3:29])[C:16]=2[CH:21]=1

Participants

7

Reactant 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 202287175-(3,7-Dimethylimidazo[1,2-a]pyridin-2-yl)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 20228701HCID 20228701, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)-2-benzothiazolinone (1.77 g) and sodium hydride (50% suspension in oil, 0.788 g) in dry dimethylformamide (24 ml) was stirred at 40° to 45° C. for 20 minutes. To the resultant mixture was added a solution of 2-diethylaminoethyl chloride hydrochloride (1.55 g) and 1.8 ml of a methanolic solution of sodium methoxide (5 mole/ml) in methanol (30 ml) at ambient temperature. The mixture was stirred for 4 hours under the same condition. The reaction mixture was poured into ice-water (300 ml) and extracted with ethyl acetate. The separated organic layer was re-extracted with 1N hydrochloric acid (25 ml) and the aqueous extract was allowed to stand for 2 hours at ambient temperature to give crystals, which was collected by filtration and dried over phosphorus pentoxide to give 5-(3,7dimethylimidazo[1,2-a]pyridin-2-yl)-3-(2-diethylaminoethyl)-2-benzothiazolinone hydrochloride (0.68 g). mp. 272° C. (dec.).

Workup

  1. stirringThe mixture was stirred for 4 hours under the same condition
  2. extractionextracted with ethyl acetate
  3. extractionThe separated organic layer was re-extracted with 1N hydrochloric acid (25 ml)
  4. extractionthe aqueous extract
  5. waitto stand for 2 hours at ambient temperature
  6. customto give crystals, which
  7. filtrationwas collected by filtration
  8. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-819bb92237a84d89b040038337727fdd
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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