Pivaloyl chloride → N-(4-nitro-3-(trifluoromethyl)phenyl)pivalamide

HRID 2404900Notes

Reaction equation

HRID 2404900 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15])=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 949554-Nitro-3-(trifluoromethyl)aniline

Product 1

HCID 9831118N-(4-nitro-3-(trifluoromethyl)phenyl)pivalamideYield 116.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-nitro-3-(trifluoromethyl)aniline (1.0 g, 4.85 mmol) in CH2Cl2 (15 mL) and TEA (2.95 g, 4.1 mL, 29.11 mmol) in a round-bottom flask at 0° C. was added trimethylacetyl chloride (1.75 g, 1.8 mL, 14.55 mmol) dropwise. The reaction mixture was warmed to room temperature and was quenched by pouring into water. The layers were separated, and the aqueous layer was extracted with DCM. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The residue was then purified by silica gel column chromatography using (0-100% EtOAc/Hex.) to obtain N-(4-nitro-3-(trifluoromethyl)phenyl)pivalamide (1.64 g, 81%). LC/MS: m/z 291.1 (M+H)+ at 1.83 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas quenched
  2. additionby pouring into water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f49686ad0d9d446ab25701c32ba1e883
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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