Methylhydrazine → Cyclopropyl-methyl-[1-methyl-5-(2-methyl-propenyl)-1H-[1,2,4]triazol-3-yl]-amine

HRID 1054937Notes

Reaction equation

HRID 1054937 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][C:4]([N:6]=C=S)=O.[CH3:10][NH:11][CH:12]1[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].I[CH3:22].[CH3:23][NH:24][NH2:25]>O1CCCC1>[CH:12]1([N:11]([CH3:10])[C:23]2[N:6]=[C:4]([CH:3]=[C:2]([CH3:9])[CH3:1])[N:25]([CH3:22])[N:24]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 5

HCID 6061MethylhydrazineHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 11029756N-MethylcyclopropanamineHCID 900170793-Methylbut-2-enoyl isothiocyanate

Product 1

HCID 90025421Cyclopropyl-methyl-[1-methyl-5-(2-methyl-propenyl)-1H-[1,2,4]triazol-3-yl]-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methylbut-2-enoyl isothiocyanate (500 mg, 3.54 mmol, Eq: 1.00) in Tetrahydrofuran (3.5 ml) was added a solution of N-methylcyclopropanamine (264 mg, 3.72 mmol, Eq: 1.05) in Tetrahydrofuran (3.5 ml). The mixture was stirred for 30 minutes. Sodium carbonate (394 mg, 3.72 mmol, Eq: 1.05) and iodomethane (1.01 g, 443 μl, 7.08 mmol, Eq: 2) was added and stirred overnight at 70° C. The solvent was evaporated. Methylhydrazine (1.63 g, 1.86 ml, 35.4 mmol, Eq: 10) was added and the mixture was stirred for 2 hours at 100° C. MS showed just product peak. The crude material was applied on silica gel and purified by column chromatography using heptane/ethyl acetate (0-40% ethyl acetate) as eluent affording

Workup

  1. stirringstirred overnight at 70° C
  2. customThe solvent was evaporated
  3. stirringthe mixture was stirred for 2 hours at 100° C
  4. custompurified by column chromatography
  5. customaffording

Sources & evidence

ORD record
ord-58110a99baba482d8cbd723bf1aef061
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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