Dimethylformamide → HCID 178424002, compound

HRID 489714Notes

Reaction equation

HRID 489714 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].CN([CH:13]=[O:14])C>O>[OH:14][C:13]1[NH:1][C:2]2[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 175932,3-Diaminotoluene

Product 1

HCID 178424002HCID 178424002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

2,3-Diaminotoluene (5 g, 41 mmol), 1,1-carbonyldiimidazole (7.3 g, 45 mmol) and 50 ml of anhydrous DMF are successively introduced into a 250 ml two-necked flask under an argon atomosphere, equipped with a magnetic stirrer. After heating the mixture at 90-95° C. for 4 hours, the solvent is distilled off under vacuum and the residue obtained is taken up in water (250 ml) and extracted with ethyl acetate (3×250 ml). The insoluble product formed during the extraction is recovered (4.8 g) and the combined organic phases are washed again with saturated NaCl solution, dried over MgSO4, filtered and concentrated, allowing a further 1.2 g of desired product (6 g, quantitative) to be recovered. 1H NMR (300 MHz, δ ppm) DMSO-d6: 2.27 (s, 3H), 6.72 (m, 2H), 6.82 (m, 1H).

Workup

  1. customequipped with a magnetic stirrer
  2. distillationthe solvent is distilled off under vacuum
  3. customthe residue obtained
  4. extractionextracted with ethyl acetate (3×250 ml)
  5. customThe insoluble product formed during the extraction
  6. customis recovered (4.8 g)
  7. washthe combined organic phases are washed again with saturated NaCl solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto be recovered

Sources & evidence

ORD record
ord-e6668013d8a24218bef0aac61d61ff73
Source dataset
uspto-grants-2005_12
Patent number
US06979683B2

Reaction notes

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