Dimethylformamide → HCID 58548623, compound

HRID 1846773Notes

Reaction equation

HRID 1846773 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8](O)=O)[CH2:4][CH2:3]1.[C:11]1([NH2:18])[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH3:19]N(C=O)C>N1C=CC=CC=1>[CH3:19][O:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:18][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 1511384-Hydroxycyclohexanecarboxylic acid

Product 1

HCID 58548623HCID 58548623, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

4-Hydroxy-cyclohexanecarboxylic acid (2 g, 13.8 mmol) in a mixture of DMF (4 mL) and pyridine (4 mL) was treated with 1,1-carbonyldiimidazole (2.26 g, 213.8 mmol) at RT and the resulting solution was stirred at 45° C. for 2 h. The mixture was treated with benzene-1,2-diamine (1.5 g, 13.8 mmol) and stirred at RT overnight. After completion, the mixture was concentrated and the obtained residue was treated with glacial acetic acid (20 mL) and heated at 110° C. for 0.5 h. The solution was allowed to cool to RT and concentrated to get a residue, which was purified by flash chromatography on silica gel to provide the title compound (3.0 g, 13.0 mmol, 71% yield) as yellow solid.

Workup

  1. stirringstirred at RT overnight
  2. concentrationAfter completion, the mixture was concentrated
  3. additionthe obtained residue was treated with glacial acetic acid (20 mL)
  4. temperatureheated at 110° C. for 0.5 h
  5. temperatureto cool to RT
  6. concentrationconcentrated
  7. customto get a residue, which
  8. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2c8e594e2fc246bda7bfdc70264744f9
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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