Dimethylformamide → HCID 22473925, compound

HRID 2183594Notes

Reaction equation

HRID 2183594 reaction equation
Br.[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3Br)=[CH:8][CH:9]=[CH:10][C:3]1=2.C([Mg]Cl)C.CN(C)[CH:26]=[O:27]>O1CCCC1>[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3[CH:26]=[O:27])=[CH:8][CH:9]=[CH:10][C:3]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22473769HCID 22473769, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 22473925HCID 22473925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

3-(Benzo[b]thiophen-4-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (1.2 g) was added in portions under nitrogen at 5-10° C. over 5 minutes to a stirred solution of ethylmagnesium chloride (2.0 M solution in ether; 4.5 ml) in tetrahydrofuran (20 ml), then the mixture was stirred at 5-15° C. for 2 hours. Dimethylformamide (1.3 ml) was added at 5-10° C. over 5 minutes, then the mixture was stirred at ambient temperature for 3 hours, cooled to 15° C. and quenched by the cautious addition of saturated aqueous ammonium chloride solution (10 ml) and water (10 ml). Ethyl acetate (20 ml) was added and the mixture was stirred at ambient temperature for 18 hours. The product was extracted into ethyl acetate (2×50 ml) and the combined extracts were washed with saturated aqueous sodium chloride solution (50 ml), dried (MgSO4), and the solvents were removed in vacuo. The residue was triturated with propan-2-ol (5 ml) and the resulting solid was collected by filtration, washed with propan-2-ol (5 ml) and dried in vacuo at 60° C. to give 3-(benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.37 g) as a brown solid which was used without further purification.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. temperaturecooled to 15° C.
  3. customquenched by the cautious addition of saturated aqueous ammonium chloride solution (10 ml) and water (10 ml)
  4. additionEthyl acetate (20 ml) was added
  5. stirringthe mixture was stirred at ambient temperature for 18 hours
  6. extractionThe product was extracted into ethyl acetate (2×50 ml)
  7. washthe combined extracts were washed with saturated aqueous sodium chloride solution (50 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvents were removed in vacuo
  10. customThe residue was triturated with propan-2-ol (5 ml)
  11. filtrationthe resulting solid was collected by filtration
  12. washwashed with propan-2-ol (5 ml)
  13. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-b6113cc0aa504b418f3881cf1185c23c
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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