Isopropanol → HCID 178431911, compound

HRID 1637640Notes

Reaction equation

HRID 1637640 reaction equation
ClC[C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=3)[N:20]=2)[CH:6]=[CH:5][N:4]=1.[SH:27][C:28]1[N:32]([C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)[N:31]=[N:30][N:29]=1.[CH:40](O)(C)C>>[CH3:9][C:8]1[C:3]([SH:27]([CH3:40])[C:28]2[N:32]([C:33]3[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=3)[N:31]=[N:30][N:29]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=2)[N:20]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 178516236HCID 178516236, compound

Product 1

HCID 178431911HCID 178431911, compoundYield 75%

Conditions

Temperature
0 °C

Procedure

0.61 g (1.5 mmol) of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine and 0.30 g (1.5 mmol) of 4-(5-mercaptotetrazol-1-yl)phenol in 30 ml of isopropanol are heated under reflux for 2 h under a nitrogen atmosphere. The mixture is then concentrated. The residue is taken up in 30 ml of water, adjusted to pH 9 using 2N sodium hydroxide solution and extracted with 4×30 ml of dichloromethane. The organic extracts are washed with water, dried over magnesium sulfate and concentrated. The residue is taken up in 200 ml of hot acetonitrile, clarified with active carbon, filtered, concentrated to a volume of 50 ml and cooled to 0° C. The precipitate is filtered off, washed with acetonitrile and dried. 0.64 g (75%) of the title compound is isolated as a pale beige solid. M.p. 92° C. (dec.).

Workup

  1. temperatureunder reflux for 2 h under a nitrogen atmosphere
  2. concentrationThe mixture is then concentrated
  3. extractionextracted with 4×30 ml of dichloromethane
  4. washThe organic extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. filtrationfiltered
  8. concentrationconcentrated to a volume of 50 ml
  9. filtrationThe precipitate is filtered off
  10. washwashed with acetonitrile
  11. customdried

Sources & evidence

ORD record
ord-c8a6881333fc46e58f1e6233c4727024
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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