Potassium Carbonate → 3-Nitro-6-tritylsulfanylimidazo[1,2-b]pyridazine

HRID 1637618Notes

Reaction equation

HRID 1637618 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[C:14]1([C:20]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[SH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[N+:11]([C:8]1[N:6]2[N:7]=[C:2]([S:21][C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 105359816-Chloro-3-nitro-imidazo(1,2-b)pyridazine

Product 1

HCID 187994273-Nitro-6-tritylsulfanylimidazo[1,2-b]pyridazineYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.0 g (40.3 mmol) of 6-chloro-3-nitroimidazo[1,2-b]pyridazine, 16.7 g (60.4 mmol) of triphenyl-methanethiol and 16.7 g (120 mmol) of potassium carbonate in 150 ml of dioxane are heated to 90° C. for 5 h under an argon atmosphere. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The residue is dissolved in a little ethyl acetate and treated with 100 ml of diisopropyl ether. After 18 h, the crystalline precipitate is filtered off and dried. 12.69 g (72%) of the title compound are isolated. M.p.: 168-170° C.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in a little ethyl acetate
  4. additiontreated with 100 ml of diisopropyl ether
  5. filtrationthe crystalline precipitate is filtered off
  6. customdried

Sources & evidence

ORD record
ord-b010311c34624781a512d519d0a50aa6
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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