2,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazole → 2,3-Dihydroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde

HRID 1585447Notes

Reaction equation

HRID 1585447 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[N:9]([CH:10]=1)[CH2:8][CH2:7][S:6]2>C(#N)C.O.[O-2].[O-2].[Mn+4]>[S:6]1[CH2:7][CH2:8][N:9]2[CH:10]=[C:3]([CH:2]=[O:1])[N:4]=[C:5]12

Participants

5

Reactant 1

HCID 181830822,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazole

Product 1

HCID 112406042,3-Dihydroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2,3-Dihydro-6-hydroxymethylimidazo[2,1-b]thiazole (1.47 g, 9.4 mmol) was dissolved in acetonitrile (30 ml) by addition of water (minimum volume). Manganese dioxide (4.41 g, 3 wt. equivalents) was added and the mixture stirred at ambient temperatures for 1.5 h. The mixture was filtered through Keiselguhr, the filter pad washed with water and the combined filtrate and washings evaporated to dryness under reduced pressure. The residue was triturated under diethyl ether, the solid collected by filtration and dried in air (1.33 g, 92%); nmax (CH2Cl2) 1685, 1528, 1272, 1260 and 1152 cm-1 ; dH (90 MHz; CD3OD) 3.84-4.10 (2H, m), 4.20-4.50 (2H, m), 7.97 (1H, s), 9.52 (1H, s).

Workup

  1. filtrationThe mixture was filtered through Keiselguhr
  2. washthe filter pad washed with water
  3. customthe combined filtrate and washings evaporated to dryness under reduced pressure
  4. customThe residue was triturated under diethyl ether
  5. filtrationthe solid collected by filtration
  6. customdried in air (1.33 g, 92%)

Sources & evidence

ORD record
ord-b808d0088e7d4005a11c003a33fb353d
Source dataset
uspto-grants-1999_08
Patent number
US05939066

Reaction notes

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