Dichloromethane → Hydrazine

HRID 2387600Notes

Reaction equation

HRID 2387600 reaction equation
[NH2:1][NH2:2].C([N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])C.[CH2:10](Cl)Cl.[CH2:13]1[CH2:17]OC[CH2:14]1>C(#N)C.CN(C=O)C.CC(C)=O.ClCCCl>[CH:8]([N:5]([CH:13]([CH3:17])[CH3:14])[CH2:6][CH3:7])([CH3:9])[CH3:10].[NH2:1][NH2:2]

Participants

10

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9321Hydrazine

Product 2

HCID 9321HydrazineHCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Alternatively, as also shown in Scheme VI, intermediate III-2 can be treated with hydrazine and an appropriate base such as triethylamine, diisopropylethylamine or excess hydrazine in a suitable organic solvent such as DCM, THF, DCE, acetone, DMF or acetonitrile to give intermediate VI-3. Intermediate VI-3 can then be treated with BrCN in the presence of a suitable base such as triethylamine, diisopropylethylamine, K2CO3, NaHCO3, or NaOAc in an appropriate organic solvent such as DCE, DCM, THF, ether, or acetonitrile at room temperature or elevated temperatures to give oxadiazole VI-4. Functionalization of the amino group affords oxadiazoles VI-5 (Arzneimittel-Forschung (2003), 53(5), 301-306; Heterocyclic Communications (2003), 9(2), 199-202; Arzneimittel-Forschung (2003), 53(1), 44-52).

Sources & evidence

ORD record
ord-b25d3cebdf714864995abda3db739244
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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