Dimethylformamide → HCID 22474161, compound

HRID 2183669Notes

Reaction equation

HRID 2183669 reaction equation
Br.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]=[C:8]([C:11]3[N:12]4[CH2:19][CH2:18][N:17]=[C:13]4[S:14][C:15]=3Br)[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[CH:7]=[C:8]([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:9]=[CH:10][C:3]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22474068HCID 22474068, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 22474161HCID 22474161, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Benzo[b]thiophen-5-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (1.9 g) was added in portions under nitrogen at 0-5° C. to a stirred solution of ethylmagnesium chloride (2M solution in ether; 6.8 ml) in tetrahydrofuran (30 ml), then the mixture was stirred at this temperature for 20 minutes. Dimethylformamide (1.5 ml) was added at <15° C., the mixture was stirred at <15° C. for 20 minutes and at ambient temperature for 1 hour, then it was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (5 ml). Ethyl acetate (30 ml) was added, the mixture was stirred at ambient temperature for 18 hours, then the organic layer was separated and further product was isolated from the aqueous layer by extraction into ethyl acetate (2×15 ml). The combined ethyl acetate solutions were washed with water (2×30 ml) and saturated aqueous sodium chloride solution (35 ml), then they were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using a 9:1 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents were removed in vacuo to give 3-(benzo[b]thiophen-5-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.7 g) as a yellow solid, m.p. 146° C.

Workup

  1. stirringthe mixture was stirred at <15° C. for 20 minutes and at ambient temperature for 1 hour
  2. customit was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (5 ml)
  3. additionEthyl acetate (30 ml) was added
  4. stirringthe mixture was stirred at ambient temperature for 18 hours
  5. customthe organic layer was separated
  6. customfurther product was isolated from the aqueous layer by extraction into ethyl acetate (2×15 ml)
  7. washThe combined ethyl acetate solutions were washed with water (2×30 ml) and saturated aqueous sodium chloride solution (35 ml)
  8. dry with materialthey were dried (MgSO4)
  9. customthe solvents were removed in vacuo
  10. customThe residue was purified by flash chromatography over silica using
  11. additiona 9:1 mixture of ethyl acetate and methanol as eluant
  12. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-17218fe4a1104b90adacfa808aecafe1
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

Loading…