Imidazo[2,1-b]thiazole-6-methanol, 2,3-dihydro-, 1,1-dioxide → HCID 18183096, compound

HRID 1636975Notes

Reaction equation

HRID 1636975 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(=[O:12])=[O:11]>C(#N)C.[O-2].[O-2].[Mn+4]>[S:6]1(=[O:12])(=[O:11])[CH2:7][CH2:8][N:9]2[CH:10]=[C:3]([CH:2]=[O:1])[N:4]=[C:5]12

Participants

4

Reactant 1

HCID 18183097Imidazo[2,1-b]thiazole-6-methanol, 2,3-dihydro-, 1,1-dioxide

Product 1

HCID 18183096HCID 18183096, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

2.3-Dihydro-6-hydroxymethylimidazo[2,1-b]thiazole-1,1-dioxide (207 mg, 1.1 mmol) was dissolved in acetonitrile (minimum volume) and treated with manganese dioxide (621 mg, 3 wt. equivalents) and the mixture stirred vigorously at ambient temperature. After 1 h, more manganese dioxide (621 mg) was added and the mixture stirred for a further 18 h. The mixture was filtered through Celite, the filter bed washed with acetonitrile, the filtrate and washings combined and evaporated to dryness under reduced pressure. The residue was triturated under dichloromethane and the resulting solid collected by filtration, washed with dichloromethane and dried in air (108 mg, 53%) (Found: M+ 186.0103. C6H6N2O3S requires M 186.0099); νmax (Nujol) 1691, 1320 and 1132 cm-1 ; δH [250 MHz; (CD3)2SO] 4.25 (2H, t, J 7 Hz), 4.68 (2H, t, J 7 Hz), 8.32 (1H, s), 9.81 (1H, s).

Workup

  1. stirringthe mixture stirred for a further 18 h
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter bed washed with acetonitrile
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was triturated under dichloromethane
  6. filtrationthe resulting solid collected by filtration
  7. washwashed with dichloromethane
  8. customdried in air (108 mg, 53%) (Found: M+ 186.0103. C6H6N2O3S requires M 186.0099)

Sources & evidence

ORD record
ord-5c4dbfad7ade4fbd96a3351083dcbfab
Source dataset
uspto-grants-2000_03
Patent number
US06037469

Reaction notes

Loading…