Sodium amide → HCID 131714672, compound

HRID 1905758Notes

Reaction equation

HRID 1905758 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-4faa28eb02084379bb46d135ef5851bb
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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