Formamide → HCID 15005406, compound

HRID 892774Notes

Reaction equation

HRID 892774 reaction equation
[CH:1]([NH2:3])=[O:2].Br[CH:5]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:6](=O)[CH3:7].C(=O)(O)[O-].[Na+]>ClCCl>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([C:5]2[O:2][CH:1]=[N:3][C:6]=2[CH3:7])=[CH:10][CH:11]=1)#[N:14]

Participants

5

Reactant 3

HCID 713FormamideHCID 516892Sodium BicarbonateHCID 15005405HCID 15005405, compound

Product 1

HCID 15005406HCID 15005406, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, two-phase mixture of formamide (0.6 ml, 15 mmol) and 4-(1-bromo-2-oxopropyl)benzonitrile (0.8 g, 3.4 mmol) was heated to 120° for 2 hours. After cooling, dichloromethane (15 ml) and saturated aqueous sodium bicarbonate (10 ml) were added, the organic phase was separated, dried (magnesium sulphate) and the solvent removed under reduced pressure to yield 0.4 g of an amorphous yellow solid. The product was purified by silica gel chromatography, eluting with dichloromethane to yield the title compound (0.29 g, 47%) as a pale yellow solid, m.p. 120°-121° C.

Workup

  1. temperaturewas heated to 120° for 2 hours
  2. temperatureAfter cooling
  3. customthe organic phase was separated
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-432de15b6c1e4ef09eeec18ab8da8498
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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