Dimethylformamide → HCID 22473695, compound

HRID 2183634Notes

Reaction equation

HRID 2183634 reaction equation
C([Li])CCC.[S:6]1[C:10]([C:11]2[N:12]3[CH2:18][CH2:17][N:16]=[C:13]3[S:14][CH:15]=2)=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2.CN(C)[CH:25]=[O:26].[Cl-].[NH4+]>O1CCCC1>[S:6]1[C:10]([C:11]2[N:12]3[CH2:18][CH2:17][N:16]=[C:13]3[S:14][C:15]=2[CH:25]=[O:26])=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 9943990HCID 9943990, compoundHCID 178418339Butyllithium

Product 1

HCID 22473695HCID 22473695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (1.6 M solution in hexanes; 6.25 ml) was added dropwise under nitrogen at −70° C. to a stirred solution of 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole (2.58 g) in tetrahydrofuran (40 ml), then the mixture was stirred at −70° C. for 10 minutes and at 0° C. for 35 minutes. Dimethylformamide (0.85 ml) was added, the mixture was stirred at 0° C. for 1.5 hours, then it was poured into saturated aqueous ammonium chloride solution (200 ml). The product was extracted into ethyl acetate (2×200 ml), then the combined extracts were washed with water (2×100 ml) and saturated aqueous sodium chloride solution (2×100 ml), dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using a 19:1 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-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.73 g) as a yellow solid which was used without further purification.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1.5 hours
  2. extractionThe product was extracted into ethyl acetate (2×200 ml)
  3. washthe combined extracts were washed with water (2×100 ml) and saturated aqueous sodium chloride solution (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvents were removed in vacuo
  6. customThe residue was purified by flash chromatography over silica using
  7. additiona 19:1 mixture of ethyl acetate and methanol as eluant
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5ce6e678b6184d0ba2e5258c1e18078c
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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