Semicarbazide hydrochloride → HCID 18958729, compound

HRID 1708429Notes

Reaction equation

HRID 1708429 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].C[O-].[Na+].[F:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([CH2:17][C:18]#[N:19])=O)=[CH:13][CH:12]=1>C(O)C>[NH2:19][C:18]1[N:3]([C:4]([NH2:6])=[O:5])[N:2]=[C:15]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:21][CH:20]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 2783172p-FluorobenzoylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 18958729HCID 18958729, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 12.0 g of semicarbazide hydrochloride in 200 ml of ethyl alcohol is added 5.35 g of sodium methoxide. The reaction mixture is stirred for 15 minutes and 16.3 g of p-fluorobenzoylacetonitrile added. The reaction mixture is heated at reflux for 2 hours, cooled and concentrated in vacuo to a separated solid which is filtered and washed with water and air dried. The solid is dissolved in 200 ml of ethyl alcohol and 5 ml of triethylamine followed by reflux for 1 hour. The volatiles are evaporated in vacuo to a solid which is filtered, washed with water and air dried to give 8.0 g of the desired product as a solid, m.p. 140° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo to a separated solid which
  5. filtrationis filtered
  6. washwashed with water and air
  7. customdried
  8. dissolutionThe solid is dissolved in 200 ml of ethyl alcohol
  9. temperatureby reflux for 1 hour
  10. customThe volatiles are evaporated in vacuo to a solid which
  11. filtrationis filtered
  12. washwashed with water and air
  13. customdried

Sources & evidence

ORD record
ord-c97b111a767a413191196971a3b31e86
Source dataset
uspto-grants-1994_10
Patent number
US05358947

Reaction notes

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