4-Azidobutyrophenone → 2-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

HRID 2189928Notes

Reaction equation

HRID 2189928 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4](=[S:7])[NH:5][NH2:6].[N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)=[N+:14]=[N-:15]>CCO.ClCCl.C(O)(=O)C>[N:13]([CH2:16][CH2:17][CH2:18][C:19]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:6][N:5]=[C:4]([C:3]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:2]=2[F:1])[S:7]1)=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 108779184-AzidobutyrophenoneHCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazide

Product 1

HCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazoleYield 54.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 2,5-difluorobenzothiohydrazide (Example 1, Steps A and B; 1.5 g, 7.97 mmol) in EtOH/dichloromethane (3:1, 16 mL) was added 4-azido-1-phenylbutan-1-one (1.36 g, 7.17 mmol). After stirring at room temperature for 16 hours, acetic acid (2 drops) was added, and the mixture was stirred for another 16 hours. The reaction mixture was then concentrated under reduced pressure and chromatographed (9:1 hexanes/ethyl acetate) to provide the product (1.41 g, 41%) as a bright yellow syrup.

Workup

  1. stirringthe mixture was stirred for another 16 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customchromatographed (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6e6491655412474b9a41aec4a5bc81c6
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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