1-Chloro-2,4-Dinitrobenzene → HCID 21260799, compound

HRID 634873Notes

Reaction equation

HRID 634873 reaction equation
[CH3:1][NH:2][CH:3]([OH:5])[CH3:4].Cl[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])O.[Na+].O>C(O)C>[N+:16]([C:8]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=1[N:2]([CH:3]([OH:5])[CH3:4])[CH3:1])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 516892Sodium BicarbonateHCID 5247031N-Methylaminoethanol

Product 1

HCID 21260799HCID 21260799, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

20.3 g of N-methylaminoethanol was dissolved in 100 ml of ethanol and, while stirring, solid 1-chloro-2,4-dinitrobenzene was added to the solution by portions at room temperature. After completion of the addition, 8.4 g of sodium hydrogencarbonate was gradually added to the reaction mixture, followed by stirring for 10-15 minutes at room temperature. Then, the reaction mixture was heated at 60° C. After completion of the reaction, the reaction solution was cooled to room temperature, and poured into 300 ml of water. Continued stirring of the solution yielded a yellowish oily product. Stirring was then discontinued and, after completion of oil formation, the supernatant was removed. After adding water thereto, the solution obtained was stirred and the oil layer formed was collected by separation, and dried to obtain a yellowish oily product. Chemical structure of the product was confirmed by 1H-NMR. Absorptivity coefficient of the product at 365 nm was measured to be 1.79×104 by UV measurement in ethanol. 1H-NMR(CDCl3), TMS standard (400 MHz): 2.22(s,1H), 3.03(s,3H), 3.62(m,2H), 3.92(m,2H), 7.24(d,1H), 8.18(d,1H), 8.63(s,1H).

Workup

  1. additionwas gradually added to the reaction mixture
  2. stirringby stirring for 10-15 minutes at room temperature
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was cooled to room temperature
  5. stirringContinued stirring of the solution
  6. customyielded a yellowish oily product
  7. stirringStirring
  8. customafter completion of oil formation, the supernatant was removed
  9. additionAfter adding water
  10. customthe solution obtained
  11. stirringwas stirred
  12. customthe oil layer formed
  13. customwas collected by separation
  14. customdried
  15. customto obtain a yellowish oily product

Sources & evidence

ORD record
ord-75b649543ddd47bb926ae70ac2121777
Source dataset
uspto-grants-2001_02
Patent number
US06184305B2

Reaction notes

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