Pivalic acid → HCID 83450273, compound

HRID 2202846Notes

Reaction equation

HRID 2202846 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](O)=O.[Br:8][C:9]1[CH:10]=[C:11]([NH:16][CH3:17])[C:12]([NH2:15])=[CH:13][CH:14]=1.O=P(Cl)(Cl)Cl>>[Br:8][C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[C:3]([C:2]([CH3:7])([CH3:6])[CH3:1])[N:16]([CH3:17])[C:11]=2[CH:10]=1

Participants

4

Reactant 3

HCID 6417Pivalic acidHCID 24813Phosphorus oxychlorideHCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

Product 1

HCID 83450273HCID 83450273, compoundYield 37.6%

Procedure

To a stirred solution of 2,2-dimethylpropionic acid (304 mg) and 4-bromo-N2-methylbenzene-1,2-diamine (400 mg) was added POCl3 (5 ml), and the mixture was heated at reflux for 4 h. The mixture was then cooled to room temperature, and poured into ice-cold saturated NaHCO3 solution. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (200 mg) as a light orange solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. additionpoured into ice-cold saturated NaHCO3 solution
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-a5d19c4483a04eec9b6b449a4a4c7ee6
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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