Ethyl trichloroacetate → N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide

HRID 2094784

Reaction equation

[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH:15][CH3:16])=[O:14])[CH:8]=2)=[CH:4][CH:3]=1.C([O:21][C:22](=O)[C:23]([Cl:26])([Cl:25])[Cl:24])C>C1(C)C=CC=CC=1>[CH3:16][NH:15][C:13](=[O:14])[C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([NH:1][C:22](=[O:21])[C:23]([Cl:26])([Cl:25])[Cl:24])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-aminophenoxy)-N-methylpicolinamide (35 g, 0.144 mol) was mixed with ethyl-2,2,2-trichloroacetate (50 ml, 0.27 mol) in toluene (350 ml) at ambient temperature. The mixture was then heated to 100° C. under distillation mode for 2-3 hours. The organic solvent was degassed under reduced pressure to obtain oil. This oil was triturated with hexane (500 ml) to obtain (49 g) of the desired solid.

Workup

customThe organic solvent was degassed under reduced pressure
customto obtain oil
customThis oil was triturated with hexane (500 ml)

Sources & evidence

ORD record: ord-284905d4c53f4ad3bcd9f9c896f6b010
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445687B2

Linked notes

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