Pivaloyl chloride → HCID 59199277, compound

HRID 2079682Notes

Reaction equation

HRID 2079682 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:4]=1[NH2:5].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:4]=1[NH:5][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 6006372-Methoxy-5-(trifluoromethyl)aniline

Product 1

HCID 59199277HCID 59199277, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methoxy-5-(trifluoromethyl) aniline (1 eq) in DCM at 0° C. was added TEA (1 eq) followed by dropwise addition of pivaloyl chloride (1 eq). The reaction mixture was warmed to room temperature and left stirred overnight. Diluted with DCM and washed with satd. sodium bicarbonate, water, brine and dried over sodium sulfate. Filtered, evaporated and dried under vacuum to provide pure product as an off white solid in 95% yield. ES/MS m/z 276.1 (MH+).

Workup

  1. waitleft
  2. washwashed with satd
  3. dry with materialsodium bicarbonate, water, brine and dried over sodium sulfate
  4. filtrationFiltered
  5. customevaporated
  6. customdried under vacuum
  7. customto provide pure product as an off white solid in 95% yield

Sources & evidence

ORD record
ord-f575f9978c394089aae2cfab5931b665
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…