Hydrochloric Acid → 5-Formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 2166997Notes

Reaction equation

HRID 2166997 reaction equation
Cl.[F:2][C:3]([F:20])([F:19])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([CH:14]2OCC[O:15]2)=[CH:11][C:12]=1[CH3:13])=[O:7]>CC(C)=O>[F:20][C:3]([F:2])([F:19])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([CH:14]=[O:15])=[CH:11][C:12]=1[CH3:13])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674294865-[1,3]Dioxolan-2-yl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Product 1

HCID 866580355-Formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 51.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

HCl (2N, 4 ml) is added to a solution of 5-[1,3]dioxolan-2-yl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (450 mg) in acetone (10 ml). After 4 hours at 50° C. and one night at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (196 mg) as a yellowish oil. MS (HPLC/MS): 252 (MH+). Retention time: 2.54 min.

Workup

  1. customone night at room temperature, the reaction is quenched with water
  2. extractionThe reaction mixture is extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-2610902fe75f4bf69d4571fee1575ff7
Source dataset
uspto-grants-2015_06
Patent number
US09044389B2

Reaction notes

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