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

HRID 1636974Notes

Reaction equation

HRID 1636974 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); νmax (nujol) 3354, 1377, 1325 and 1133 cm-1 ; δH [250 MHz; (CD3)2SO] 4.14 (2H, t, J 6 Hz), 4.40 (2H, d, J 6 Hz), 4.54 (2H, t, J 6 Hz), 5.20 (1H, t, J 6 Hz, 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-397ff84943824be089b396e0caaefe4c
Source dataset
uspto-grants-2000_03
Patent number
US06037469

Reaction notes

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