2-Chloroethyl methyl sulfide → HCID 18005372, compound

HRID 989243Notes

Reaction equation

[H-].[K+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([NH2:20])=[C:18]([S:21]([CH2:23][CH3:24])=[O:22])[C:17]([C:25]#[N:26])=[N:16]1.[CH3:27][S:28][CH2:29][CH2:30]Cl.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([NH:20][CH2:30][CH2:29][S:28][CH3:27])=[C:18]([S:21]([CH2:23][CH3:24])=[O:22])[C:17]([C:25]#[N:26])=[N:16]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 35% potassium hydride in oil (1.4 g) in dry N,N-dimethylformamide (DMF) was added a solution of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-amino-4-(ethylsulfinyl)-1H-pyrazole-3-carbonitrile (5.0 g) in dry DMF at 4° C. and stirred for 40 min. 2-Chloroethyl methyl sulfide (1.39 g) was added at 4° C. and the stirred mixture allowed to warm to 20° C. over 40 minutes, then heated to 50° C. for 4 hours and at 20° C. for 3 days. Ammonium chloride solution and ethyl acetate were added and the organic layer dried (sodium sulfate), evaporated and purified by column chromatography using 80% methyl t-butyl ether in hexane to give 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[[-2-(methylthio)ethyl]amino]-4-(ethylsulfinyl)-1H-pyrazole-3-carbonitrile (0.26 g), m.p.126-127° C.

Workup

temperatureheated to 50° C. for 4 hours and at 20° C. for 3 days
dry with materialthe organic layer dried (sodium sulfate)
customevaporated
custompurified by column chromatography

Sources & evidence

ORD record: ord-456ae4ad2df34008a073c8d8bf4e9327
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638956B2

Reaction notes

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