1-Amino-2-propanol → HCID 86599994, compound

HRID 2103414Notes

Reaction equation

HRID 2103414 reaction equation
Br[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].[NH2:28][CH2:29][CH:30]([OH:32])[CH3:31].C(N(CC)CC)C>O1CCOCC1>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:28][CH2:29][CH:30]([OH:32])[CH3:31])=[C:3]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

5

Reactant 3

HCID 41-Amino-2-propanolHCID 8471TriethylamineHCID 167270545-Bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

Product 1

HCID 86599994HCID 86599994, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole (3.0 g, 5.8 mmol) in 1,4-dioxane was added 1-amino-2-propanol (0.52 g, 7.0 mmol) and triethylamine (0.76g, 7.5 mmol). The mixture was heated at 100° C. for 2 hours. After extractive workup and recrystallisation from heptane-ethyl acetate (1:1) there was obtained 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(2-hydroxypropylamino)-4-trifluoromethylsulfonylpyrazole (Compound number 1-5, 2.67 g), 19F: −64.2; −80.9.

Workup

  1. customAfter extractive workup and recrystallisation from heptane-ethyl acetate (1:1) there

Sources & evidence

ORD record
ord-8afaa8035364400099c03558206414fd
Source dataset
uspto-grants-2009_08
Patent number
US07576107B2

Reaction notes

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