Ethanethiol → 6-Ethylthio-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonamide

HRID 1946456Notes

Reaction equation

HRID 1946456 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:15]([NH2:18])(=[O:17])=[O:16])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[N:7]=1.CC(C)([O-])C.[K+].[CH2:25]([SH:27])[CH3:26]>C(O)(C)(C)C>[CH2:25]([S:27][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:15]([NH2:18])(=[O:17])=[O:16])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[N:7]=1)[CH3:26]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 230281086-Chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazine-3-sulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 230281186-Ethylthio-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonamide

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

6-Chloro-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonamide (1.00 g, 3.33 mmol) was suspended in t-butyl alcohol (20.0 ml) and stirred at room temperature, during which potassium t-butoxide (80%, 1.40 g, 9.98 mmol) and ethanethiol (0.54 ml, 7.29 mmol) were added thereto. After the mixture was heated for 4 hours under reflux, the reaction solution was left and cooled to room temperature, poured into ice-water (200 ml) and adjusted to pH 3. The precipitated crystals were filtered and washed with water to give the title compound as colorless crystals. The yield was 0.54 g (50.0%).

Workup

  1. additionwere added
  2. temperatureAfter the mixture was heated for 4 hours
  3. temperatureunder reflux
  4. waitthe reaction solution was left
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-b50e8a88c9414e958167bbf580699d69
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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