Sodium amide → HCID 131714672, compound

HRID 280183Notes

Reaction equation

HRID 280183 reaction equation
[C:1]([CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1Br)[CH3:5])#[N:2].[NH2-].[Na+]>N>[C:1]([CH:3]1[C:11]2=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=[C:6]2[CH:4]1[CH3:5])#[N:2]

Participants

4

Reactant 2

HCID 24533Sodium amideHCID 13711147HCID 13711147, compound

Product 1

HCID 131714672HCID 131714672, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The bromo compound of Step 3. above (60.4 g) is added dropwise to a refluxing solution of sodium amide (39.0 g) in liquid ammonia (600 ml) over a period of 30 min. The mixture is refluxed for three hours, quenched with ammonium chloride (50.8 g) and evaporated. The residue is taken up in H2O, extracted with CHCl3, the CHCl3 extract is washed with 5% aq. HCl, sat'd NaCl, dried and filtered. The filtrate is stirred with silica gel, filtered and the filtrate evaporated in vacuo yielding the desired product as an oil.

Workup

  1. temperatureThe mixture is refluxed for three hours
  2. customquenched with ammonium chloride (50.8 g)
  3. customevaporated
  4. extractionextracted with CHCl3
  5. extractionthe CHCl3 extract
  6. washis washed with 5% aq. HCl
  7. customdried
  8. filtrationfiltered
  9. filtrationfiltered
  10. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6956b57ff13245d79aa21bca231de84d
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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