Formamide → HCID 10029751, compound

HRID 1613507Notes

Reaction equation

HRID 1613507 reaction equation
FC(F)(F)S([O:6][CH2:7][C:8]([C:10]1[CH:37]=[CH:36][C:13]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:32]=[CH:31][C:22]3[CH2:23][CH2:24][CH:25]([C:27]([O:29][CH3:30])=[O:28])[O:26][C:21]=3[C:20]=2[CH2:33][CH2:34][CH3:35])=[C:12]([CH2:38][CH2:39][CH3:40])[C:11]=1[O:41][CH3:42])=O)(=O)=O.[CH:45]([NH2:47])=O.CN(C)C=O>C(OCC)(=O)C.O>[CH3:42][O:41][C:11]1[C:12]([CH2:38][CH2:39][CH3:40])=[C:13]([CH:36]=[CH:37][C:10]=1[C:8]1[N:47]=[CH:45][O:6][CH:7]=1)[O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]2[CH2:23][CH2:24][CH:25]([C:27]([O:29][CH3:30])=[O:28])[O:26][C:21]=2[C:20]=1[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 713FormamideHCID 6228DimethylformamideHCID 15015342HCID 15015342, compound

Product 1

HCID 10029751HCID 10029751, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The compound of Example 3 (0.10 g, 0.155 mmol) was stirred with 0.5 ml of formamide and 0.2 ml of dimethyl formamide (DMF) for 1.5 hours at 170° C. The reaction mixture was cooled and poured into ethyl acetate/water. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was flash chromatographed on silica gel using 10:1 to 4:1 hexane/ethyl acetate eluant to give the product, 0.057 g (0.109 mmol), 35%.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customchromatographed on silica gel using 10:1 to 4:1 hexane/ethyl acetate eluant
  6. customto give the product, 0.057 g (0.109 mmol), 35%

Sources & evidence

ORD record
ord-99ce88543137437f90e59ebbf9849ff2
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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