2-(Methylamino)ethanol → HCID 86611439, compound

HRID 1360980Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[N:12]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:11]=[C:10]([C:25]#[N:26])[C:9]=1[S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28].[CH3:34][NH:35][CH2:36][CH2:37][OH:38].[Cl-].[NH4+]>CN(C)C=O>[Cl:24][C:14]1[CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:18]([Cl:19])[C:13]=1[N:12]1[C:8]([N:35]([CH2:36][CH2:37][OH:38])[CH3:34])=[C:9]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[C:10]([C:25]#[N:26])=[N:11]1

Participants

Conditions

Temperature: 20 °C

Procedure

Finely powdered potassium carbonate (7.29 g, 52.2 mmol) was added to a solution of 5-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulphonylpyrazole (10.00 g, 19.3 mmol) in dry N,N-dimethylformamide (85 ml) and stirred for 1 hour at 20° C. 2-(Methylamino)ethanol (3.11 ml, 38.7 mmol) was then added and stirring continued for 2 hours at 20° C. The resulting mixture was poured into saturated ammonium chloride solution, extracted with ethyl acetate, and the organic layer washed with water and brine, dried (sodium sulfate), evaporated and purified by column chromatography eluting with hexane and ethyl acetate (2:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(2-hydroxyethyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a fine white powder (5.65 g, yield 57%), 19F-NMR: −63.7, −78.4.

Workup

stirringstirring
waitcontinued for 2 hours at 20° C
extractionextracted with ethyl acetate
washthe organic layer washed with water and brine
dry with materialdried (sodium sulfate)
customevaporated
custompurified by column chromatography
washeluting with hexane and ethyl acetate (2:1)

Sources & evidence

ORD record: ord-75b08a974a034458b20d6774f4fd8095
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879897B2

Reaction notes

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