1,1'-Carbonyldiimidazole → (2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)(1H-imidazol-1-yl)methanone

HRID 468082Notes

Reaction equation

HRID 468082 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:11][N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3].[C:26](N1C=CN=C1)([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)=[O:27]>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]([C:26]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[O:27])[N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Product 1

HCID 86604844(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)(1H-imidazol-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (0.492 g, 1.37 mmol) in THF (8 mL) was added 1,1′-carbonyl diimidazole (0.266 g, 1.64 mmol). After stirring at 75° C. for 2 hours, the reaction mixture was concentrated under reduced pressure and dissolved in dichloromethane (20 mL). The solution was washed with HCl (0.5 M), dried over Na2SO4 and concentrated to provide the crude product.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in dichloromethane (20 mL)
  3. washThe solution was washed with HCl (0.5 M)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f1a7fa1c10c4782bbf3ae29bfc947cc
Source dataset
uspto-grants-2014_01
Patent number
US08623895B2

Reaction notes

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