Sodium Hydroxide → 3-Chloro-2-(4-chloro-3-dimethylaminothiocarbonyloxyphenyl)-5-trifluoromethylpyridine

HRID 1957251Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([OH:19])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[S:23].[H-].[Na+].[OH-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][C:22]([N:21]([CH3:25])[CH3:20])=[S:23])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 65.0 g of 3-chloro-2-(4-chloro-3-hydroxyphenyl)-5-trifluoromethylpyridine in 200 ml of dimethylformamide, and then 31.3 g of dimethylthiocarbamoyl chloride, were added dropwise to a suspension of 6.7 g of 80% sodium hydride in 300 ml of anhydrous dimethylformamide. The solution was stirred at 80° C. for one hour and then poured into 2.5 1 of 1% by weight sodium hydroxide solution. After extraction three times with 250 ml of tert-butyl methyl ether each time the combined organic phases were washed twice with 150 ml of water each time and then dried over sodium sulfate and concentrated until crystallization started. After removal of the crystals, the mother liquor was concentrated further until more of the product started to crystallized out.

Workup

extractionAfter extraction three times with 250 ml of tert-butyl methyl ether each time the combined organic phases
washwere washed twice with 150 ml of water each time
dry with materialdried over sodium sulfate
concentrationconcentrated until crystallization
customAfter removal of the crystals
concentrationthe mother liquor was concentrated further until more of the product
customto crystallized out

Sources & evidence

ORD record: ord-33873b7af43944a18b7fe038a6690831
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783522

Reaction notes

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