Methylhydrazine sulfate → 1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

HRID 631482Notes

Reaction equation

HRID 631482 reaction equation
[NH2:1]/[C:2](/OCC)=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].S(O)(O)(=O)=O.[CH3:18][NH:19][NH2:20]>>[CH3:18][N:19]1[C:4]([C:5]([F:8])([F:7])[F:6])=[CH:3][C:2]([NH2:1])=[N:20]1

Participants

3

Reactant 2

HCID 165286Methylhydrazine sulfateHCID 151117544-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 229127981-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amineYield 23.1%

Procedure

Using the procedure described in Example 161A Step 3, (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (1.83 g, 10 mmol) and methylhydrazine sulfate (1.586 g, 11 mmol) were reacted and the crude product purified by silica gel chromatography (with 0-10% EtOAc/CH2Cl2 as eluants) to afford 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine as solid (0.381 g, 23%). 1H NMR (300 MHz, CDCl3) δ 5.94 (s, 1H), 3.78 (s, 3H), 3.67 (br, 2H); LC-MS (ESI) m/z 166 (M+H)+.

Workup

  1. customwere reacted
  2. customthe crude product purified by silica gel chromatography (with 0-10% EtOAc/CH2Cl2 as eluants)

Sources & evidence

ORD record
ord-b7e59d1a81344a26af4f10a1353fbf60
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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