3-Nitrophenyl isocyanate → HCID 20073707, compound

HRID 621411Notes

Reaction equation

HRID 621411 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([N:21]=[C:22]=[O:23])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>C(#N)C.CN(C)C=O>[N+:12]([C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:23])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:6][CH:7]=2)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

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

Product 1

HCID 20073707HCID 20073707, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×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 dissolve it therein, and the resulting solution was cooled to -5° C. 65.6 g of metanitrophenyl isocyanate dissolved in 200 ml of acetonitrile was added dropwise. During this period, the mixture was stirred while cooling so that the temperature did not exceed -5° C. In addition, 300 ml of acetonitrile was added, and the resulting mixture was stirred at 0° C. for 3 hours. Crystals formed were filtered off and wash with acetonitrile and then washed with methanol. The crystals thus obtained were dissolved in 1 liter of N,N-dimethylformamide. An insoluble portion was filtered off. To the filtrate, 3 liters of methanol was added, and the resulting solution was cooled to thereby form crystals. These crystals were filtered off and washed with acetonitrile and then washed with methanol. The yield was 98.5 g.

Workup

  1. dissolutionto dissolve it
  2. additionwas added dropwise
  3. waitDuring this period
  4. temperaturewhile cooling so that the temperature
  5. customdid not exceed -5° C
  6. stirringthe resulting mixture was stirred at 0° C. for 3 hours
  7. customCrystals formed
  8. filtrationwere filtered off
  9. washwash with acetonitrile
  10. washwashed with methanol
  11. customThe crystals thus obtained
  12. filtrationAn insoluble portion was filtered off
  13. additionTo the filtrate, 3 liters of methanol was added
  14. temperaturethe resulting solution was cooled
  15. customto thereby form crystals
  16. filtrationThese crystals were filtered off
  17. washwashed with acetonitrile
  18. washwashed with methanol

Sources & evidence

ORD record
ord-44b027412a5c417da91a6bf0d2d1ffc8
Source dataset
uspto-grants-1989_04
Patent number
US04824764

Reaction notes

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