Dimethyl Sulfide → (1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride

HRID 1842886Notes

Reaction equation

HRID 1842886 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]#[N:15])=[CH:12][C:11]([C:16]([F:19])([F:18])[F:17])=[N:10]1.S(C)C.CCOCC.Cl.C(Cl)(Cl)Cl.CO>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH2:14][NH2:15])=[CH:12][C:11]([C:16]([F:18])([F:19])[F:17])=[N:10]1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 10953452Ether hydrochlorideHCID 21584188Chloroform methanolHCID 708161751-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

Product 1

HCID 86672141(1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (5.02 g, 16.46 mmol, 1.0 eq.) in THF (50 mL) was added BH3.S(CH3)2 (3.74 g, 49.38 mmol, 3.0 eq.) at 0° C. and heated to reflux for 1 h. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and basified with 1N solution of NaOH to a pH of ˜10 and extracted with ethyl acetate (100 mL×2), dried (Na2SO4), the solvent evaporated to get a pale yellow oil. The oil was treated with ether HCl to get (1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (1.15, 27% yield over 3 steps) as a white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.55).

Workup

  1. temperatureto reflux for 1 h
  2. customquenched with 1N HCl
  3. extractionextracted with ethyl acetate (100 mL×2)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated
  6. customto get a pale yellow oil

Sources & evidence

ORD record
ord-016ba02646af45368b0fb8e7a5b45290
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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