Potassium Carbonate → 7-[2-(4-Morpholinyl)ethoxy]-2-(4-nitrophenyl)imidazo[2,1-b]benzothiazole

HRID 926016Notes

Reaction equation

HRID 926016 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[N:16]([CH:17]=2)[C:15]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=2[S:13]3)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[N:27]1([CH2:26][CH2:25][O:22][C:20]2[CH:19]=[CH:18][C:15]3[N:16]4[CH:17]=[C:10]([C:7]5[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=5)[N:11]=[C:12]4[S:13][C:14]=3[CH:21]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 299332572-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol

Product 1

HCID 445987167-[2-(4-Morpholinyl)ethoxy]-2-(4-nitrophenyl)imidazo[2,1-b]benzothiazole

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol, 4-(2-chloroethyl)-morpholine hydrochloride, potassium carbonate, and tetrabutylammonium iodide were added to N,N-dimethylformamide forming a yellow suspension that was heated at a temperature of >50° C. for over 3 hours. The reaction was cooled and the solids were collected, slurried into water, filtered, slurried into acetone, filtered and washed with acetone to give yellow solids that were dried under vacuum to give 7-(2-morpholin-4-yl-ethoxy)-2-(4-nitrophenyl)imidazo[2,1-b]benzothiazole.

Workup

  1. temperaturewas heated at a temperature of >50° C. for over 3 hours
  2. temperatureThe reaction was cooled
  3. customthe solids were collected
  4. filtrationfiltered
  5. filtrationfiltered
  6. washwashed with acetone
  7. customto give yellow solids that
  8. customwere dried under vacuum

Sources & evidence

ORD record
ord-2a73c328bdad4b66b491f07bb6a3f1c4
Source dataset
uspto-grants-2016_03
Patent number
US09284332B2

Reaction notes

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