5-Chloro-2-hydroxy-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide → 5-Chloro-N-(2,2-dichloroethenyl)-2-hydroxybenzamide

HRID 973208Notes

Reaction equation

O[CH:2]([NH:7][C:8](=[O:17])[C:9]1[C:10](=[CH:12][CH:13]=[C:14]([Cl:16])[CH:15]=1)[OH:11])[C:3](Cl)([Cl:5])[Cl:4]>C(O)(=O)C.[Zn]>[Cl:5][C:3]([Cl:4])=[CH:2][NH:7][C:8](=[O:17])[C:9]1[C:10](=[CH:12][CH:13]=[C:14]([Cl:16])[CH:15]=1)[OH:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Thirty (30) g (0.09 mol) of N-(1'-hydroxy-2',2',2'-trichloroethyl)-5-chlorosalicylamide were dissolved in 150 ml of acetic acid. Nine point two (9.2) g (0.14 mol) of zinc powder were added into the solution under stirring at the temperature from 20° C to 40° C and the reaction was continued for 4 hours at the same temperature. The temperature was finally raised at 80° C and then excess zinc was removed by filtration. The filtrate was cooled to obtain 28g of crystals of N-(2',2'-dichlorovinyl)5-chloro salicylamide was obtained. Melting point of it was 208° C-210° C.

Workup

customexcess zinc was removed by filtration
temperatureThe filtrate was cooled

Sources & evidence

ORD record: ord-78d4a3cc191d49a88c09bf54fcb66c14
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04055640

Reaction notes

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