Ammonia → Imidazo[2,1-b]thiazole-6-methanol, 2,3-dihydro-, 1,1-dioxide

HRID 1416138Notes

Reaction equation

HRID 1416138 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]2[N:12]([CH:13]=1)[CH2:11][CH2:10][S:9]2(=[O:15])=[O:14])(=O)C.N>>[OH:4][CH2:5][C:6]1[N:7]=[C:8]2[N:12]([CH:13]=1)[CH2:11][CH2:10][S:9]2(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 18183092HCID 18183092, compound

Product 1

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

Procedure

6-Acetoxymethyl-2,3-dihydroimidazo[2,1-b]thiazole-1,1-dioxide (305 mg, 1.33 mmol) was treated with methanolic ammonia (prepared by saturating methanol (20 ml) with ammonia gas then diluting with more methanol (20 ml)) at room temperature. After 2.5 h, the volatiles were removed under reduced pressure and the residue triturated with diethyl ether and the resulting solid collected by filtration, washed with diethyl ether and dried in air (207 mg, 83%) (Found: M+ 188.0256. C6H8N2O3S requires M 188.0256); nmax (nujol) 3354, 1377, 1325 and 1133 cm-1 ; dH [250 MHz; (CD3)2SO] 4.14 (2H, t, J 6Hz), 4.40 (2H, d, J 6Hz), 4.54 (2H, t, J 6Hz), 5.20 (1H, t, J 6Hz, exchangeable), 7.36 (1H, s).

Workup

  1. customprepared
  2. concentrationby saturating methanol (20 ml) with ammonia gas
  3. additionthen diluting with more methanol (20 ml)) at room temperature
  4. customthe volatiles were removed under reduced pressure
  5. customthe residue triturated with diethyl ether
  6. filtrationthe resulting solid collected by filtration
  7. washwashed with diethyl ether
  8. customdried in air (207 mg, 83%) (Found: M+ 188.0256. C6H8N2O3S requires M 188.0256)

Sources & evidence

ORD record
ord-f69eaff3f92e420d9c0af0922e1325f8
Source dataset
uspto-grants-1999_06
Patent number
US05911985

Reaction notes

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