Hydrazine → 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbothioamide

HRID 2387627Notes

Reaction equation

HRID 2387627 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:11]([C:12]([NH:14]C(=O)C2C=CC=CC=2)=[S:13])[N:10]=[C:9]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[S:8]1)=[N+:2]=[N-:3].NN>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:11]([C:12](=[S:13])[NH2:14])[N:10]=[C:9]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[S:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86608769N-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole-3-carbonothioyl)benzamide

Product 1

HCID 866087702-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbothioamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole-3-carbonothioyl)benzamide (0.737 g, 1.41 mmol) in 20 mL of anhydrous THF was added hydrazine (0.088 mL, 2.82 mmol). The reaction was stirred at room temperature for 3 hours, then concentrated in vacuo. The residue was purified by flash column chromatography (10-20% ethyl acetate/hexanes) to afford the desired product as a pale yellow foam, 0.504 g, 85%.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e6c3b67214e94db4b656b617bc107fa5
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

Loading…