Dimethylformamide → HCID 70922597, compound

HRID 524990Notes

Reaction equation

HRID 524990 reaction equation
[H-].[Na+].[C:3]1([CH3:17])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)=[O:11].S([O-])([O-])(=O)=S.[Na+].[Na+].C[N:26](C=O)C>>[NH2:26][N:16]1[CH:15]=[CH:14][N:13]=[C:12]1[C:10]([NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:17])=[O:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 13022727HCID 13022727, compound

Product 1

HCID 70922597HCID 70922597, compoundYield 55%

Conditions

Temperature
0 °C

Procedure

240 mg (6.02 mmol) of sodium hydride (60% dispersion in mineral oil) were added to a 0° C. cooled solution of N-o-tolyl-1H-imidazole-2-carboxamide (0.93 g, 4.63 mmol) in DMF (120 mL). The mixture was stirred at 0° C. for 30 minutes and DPPONH2 (1.51 g, 6.49 mmol, available from Sigma Aldrich®, cat. no. 5994-87-6) was added portionwise. The mixture was stirred at room temperature for 2 hours and then it was poured into 200 mL of a saturated aqueous solution of sodium thiosulphate and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude product was purified by flash chromatography (20% to 50% AcOEt/Hexanes) to yield 0.55 g (55%) of the title compound as a beige solid.

Workup

  1. addition5994-87-6) was added portionwise
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (20% to 50% AcOEt/Hexanes)

Sources & evidence

ORD record
ord-b85e9ff56e5d46989222f40cc744e252
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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