Mesitylacetic acid → HCID 59202092, compound

HRID 1665223

Reaction equation

HRID 1665223 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10](O)=O.[CH3:14][NH:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:23]>O1CCCC1>[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]1[N:15]([CH3:14])[C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][C:17]=2[N:23]=1

Participants

4

Reactant 2

HCID 78123Mesitylacetic acidHCID 12296380N2-Methylbenzene-1,2,3-triamine

Product 1

HCID 59202092HCID 59202092, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of mesityleneacetic acid (904 mg, 5.08 mmol) in tetrahydrofuran (20 mL) was added N,N′-carbonyldiimidazole (823 mg, 5.08 mmol) at room temperature. After the mixture was stirred for 1 hr at 50° C., N2-methylbenzene-1,2,3-triamine (700 mg, 5.08 mmol) in tetrahydrofuran (8 mL) was added to the mixture and the mixture was refluxed for further 18 hr. After the mixture was cooled, the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography eluting with a 60-80% ethyl acetate/n-hexane gradient mixture to give the title compound (340 mg, 1.22 mmol, 24%) as a colorless solid. The resulting solid was recrystallized from n-hexane/tetrahydrofuran to give the title compound (254 mg, 0.85 mmol).

Workup

  1. temperaturethe mixture was refluxed for further 18 hr
  2. temperatureAfter the mixture was cooled
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with a 60-80% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-85a59076c5af4bc390c012d307e8c859
Source dataset
uspto-grants-2011_10
Patent number
US08039500B2

Linked notes

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