Dimethylformamide → HCID 20073707, compound

HRID 704311Notes

Reaction equation

HRID 704311 reaction equation
CN(C)C=O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][NH:14][CH:15]=[O:16])=[CH:9][CH:8]=1.[N+:17]([C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[O:28])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]>C(#N)C>[N+:17]([C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:28])[NH:6][C:7]2[CH:8]=[CH:9][C:10]([NH:13][NH:14][CH:15]=[O:16])=[CH:11][CH:12]=2)[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 768353-Nitrophenyl isocyanateHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 20073707HCID 20073707, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
-5 °C

Procedure

200 ml of acetonitrile and 200 ml of N,N-dimethylformamide were added to 60.4 g of 2-(4-aminophenyl)-1-formylhydrazine to be dissolved, followed by cooling to -5° C. 65.6 g of metanitrophenyl isocyanate dissolved in 200 ml of acetonitrile was added dropwise thereto. During this dropwise addition, the solution was cooled with stirring so that the temperature thereof would not exceed -5° C. A further 300 ml of acetonitrile was added at 0° C., and after stirring for 3 hours, formed crystals were filtered and washed with acetonitrile and then with methanol. The thus-obtained crystals were dissolved in 1 liter of N,N-dimethylformamide, the undissolved portion was filtered off, and 3 liters of methanol was added to the filtrate, followed by cooling to form crystals. The thus-formed crystals were then filtered and washed with acetonitrile and then methanol. The yield was 98.5 g.

Workup

  1. dissolutionto be dissolved
  2. additionwas added dropwise
  3. additionDuring this dropwise addition
  4. temperaturethe solution was cooled
  5. customexceed -5° C
  6. stirringafter stirring for 3 hours
  7. customformed crystals
  8. filtrationwere filtered
  9. washwashed with acetonitrile
  10. dissolutionThe thus-obtained crystals were dissolved in 1 liter of N,N-dimethylformamide
  11. filtrationthe undissolved portion was filtered off
  12. addition3 liters of methanol was added to the filtrate
  13. temperatureby cooling
  14. customto form crystals
  15. filtrationThe thus-formed crystals were then filtered
  16. washwashed with acetonitrile

Sources & evidence

ORD record
ord-9a11ec150faf4b7ea41c618b6f9a2dce
Source dataset
uspto-grants-1991_01
Patent number
US04987052

Reaction notes

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