1H-1,2,4-Triazole → HCID 59553048, compound

HRID 888244Notes

Reaction equation

HRID 888244 reaction equation
Cl[CH2:2][C:3]1[N:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])[N:8]=[C:5]2[S:6][CH:7]=1.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Na+].[I-]>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:8]=[C:5]2[N:4]([CH:10]=1)[C:3]([CH2:2][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)=[CH:7][S:6]2)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 59679997HCID 59679997, compound

Product 1

HCID 59553048HCID 59553048, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Chloromethyl-6-(2-nitro-phenyl)-imidazo[2,1-b]thiazole (64.0 g, 0.22 mol) was dissolved in DMF (600 mL), followed by the addition of 1H-[1,2,4]triazole (30.4 g, 0.44 mol), K2CO3 (91.0 g, 0.66 mol) and NaI (20 mg). The reaction mixture was stirred at room temperature overnight, and then at 35° C. (8 h). The mixture was passed through a silica gel pad, and the filtrate was concentrated in vacuo to give a yellow solid. The solid was washed with ethyl acetate to give 6-(2-nitro-phenyl)-3-[1,2,4]triazol-1-ylmethyl-imidazo[2,1-b]thiazole as a yellow solid (54 g, 75% yield). 1H-NMR (DMSO-d6, 400 MHz): δ 5.75 (s, 2H), 7.40 (s, 1H), 7.52 (m, 1H), 7.68 (m, 1H), 7.79 (m, 2H), 8.05 (s, 1H), 8.19 (s, 1H), 8.83 (s, 1H).

Workup

  1. customat 35° C.
  2. custom(8 h)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a yellow solid
  5. washThe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-231df408f9ba48018b5badee6d3e5b9f
Source dataset
uspto-grants-2012_08
Patent number
US08247565B2

Reaction notes

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