Formamide → HCID 15005406, compound

HRID 1460314Notes

Reaction equation

HRID 1460314 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-b3fb7e4c094a4ddb91ecb6f8f9c030b0
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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