P-Anisidine → Imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine

HRID 1043664Notes

Reaction equation

HRID 1043664 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1>C(O)C(F)(F)F.ClCCl>[S:6]1[C:2]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:3][N:4]2[CH:9]=[CH:8][N:7]=[C:5]12

Participants

5

Reactant 2

HCID 7732P-AnisidineHCID 436679232-Bromoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 67334626Imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amineYield 29.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64092,2,2-TrifluoroethanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (1.0 g, 4.90 mmol) and p-anisidine (19.6 mmol, 2.41 g) in trifluoroethanol (12 mL) was heated under microwave irradiation at 170° C. for 1 hour. On cooling, the mixture was diluted with dichloromethane (10 mL) and purified by column chromatography (Biotage™/Flash, silica, methanol: dichloromethane 0.2:9.8 to 1:9). The residue obtained was triturated with diethylether and few drops of methanol to give imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine as a white solid (355 mg, 29% yield).

Workup

  1. temperatureOn cooling
  2. custompurified by column chromatography (Biotage™/Flash, silica, methanol: dichloromethane 0.2:9.8 to 1:9)
  3. customThe residue obtained
  4. customwas triturated with diethylether and few drops of methanol

Sources & evidence

ORD record
ord-66b469d9d5f746689bf8c437c37a2dea
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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