Hydrochloric Acid → HCID 86742629, compound

HRID 414662

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[Na].Cl[C:15]1[CH:16]=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:19][C:20]=1Cl.[ClH:26]>CS(C)=O.[Cu]>[Cl:26][C:18]1[CH:19]=[C:20]([O:12][C:10]2[CH:11]=[C:4]([OH:3])[C:5](=[CH:8][CH:9]=2)[C:6]#[N:7])[CH:15]=[CH:16][C:17]=1[C:22]([F:25])([F:24])[F:23]

Participants

Conditions

Temperature: 115 °C

Procedure

To a suspension of 19.2 g of sodium hydride in 400 ml of dimethyl sulphoxide is added dropwise a solution of 54.0 g of 2,4-dihydroxybenzonitrile in 200 ml of dimethyl sulphoxide. After formation of the sodium salt 86.0 g of 3,4-dichloro-α,α,α-trifluorotoluene and 0.1 g of copper powder are added and the reaction mixture is stirred at 115° C. for 68 hours. Then the mixture is poured onto 2 kg of ice and the aqueous mixture acidified with concentrated hydrochloric acid and extracted severl times with 500 ml portions of ethyl acetate. The combined organic phases are neutralized and dried over anhydrous sodium sulphate, and the solvent is evaporated off under reduced pressure. Finally, the residue is prified by column chromatographyon silica gel using ethyl acetate / n-hexane (7:3) as the eluent and crystallized from methylene chloride. There is obtained the intermediate 4-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]-salicylonitrile, m.p. 155°-156° C.; mass spectrum; m/e 313, 294, 278, 250,223, 209, 90, 63; infrared spectrum: main peak at 2230 cm-1.

Workup

extractionextracted severl times with 500 ml portions of ethyl acetate
dry with materialdried over anhydrous sodium sulphate
customthe solvent is evaporated off under reduced pressure
customcrystallized from methylene chloride

Sources & evidence

ORD record: ord-26844c7f84814b4eab0fb341676c0f7a
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792616

Linked notes

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