Hydrazine → HCID 86608777, compound

HRID 2387622Notes

Reaction equation

HRID 2387622 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]([N:33]1C=CN=C1)(N1C=CN=C1)=[S:27].[NH2:38]N>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](=[S:27])[NH:33][NH2:38])[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

5

Reactant 3

HCID 9321HydrazineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Product 1

HCID 86608777HCID 86608777, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (577 mg, 1.61 mmol) was dissolved in 8 mL THF, followed by addition of thio-carbonyldiimidazole (458 mg, 2.57 mmol), and heated to reflux for 1 hour. The reaction mixture was cooled to 23° C., and hydrazine (257 mg, 8.03 mmol) was added. The reaction mixture was stirred for 12 hours. The crude reaction mixture was then concentrated and purified by flash column chromatography, eluting with 4:1 (hexanes/ethyl acetate), to afford the desired product (135 mg, 20%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customThe crude reaction mixture
  4. concentrationwas then concentrated
  5. custompurified by flash column chromatography
  6. washeluting with 4:1 (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-458c571ea36842798ba592835a0989ea
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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