1-Chloro-2,4-Dinitrobenzene → HCID 23048845, compound

HRID 2106778Notes

Reaction equation

HRID 2106778 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[ClH:14].[N+:21]([C:18]1[CH:17]=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=[CH:20][C:19]=1[N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5]1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 10340Sodium CarbonateHCID 92467p-(1-Piperazinyl)phenol

Product 1

HCID 23048845HCID 23048845, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4.5 parts of 4-(1-piperazinyl)phenol, 5.5 parts of 1-chloro-2,4-dinitrobenzene, 2.6 parts of sodium carbonate and 90 parts of N,N-dimethylacetamide was stirred overnight at 50° C. After cooling, the mixture was poured into ice water and the product was extracted twice with 4-methyl-2-pentanone. The undissolved product was dissolved in 2-propanol. This solution and the combined organic layers were washed with water, dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and crystallized twice: first from a mixture of 2-propanol and water (10:1 by volume) and then from a mixture of methanol and water (10:1 by volume). The product was filtered off and dried, yielding 3.9 parts (37.7%) of 4-[4-(2,4-dinitrophenyl)-1-piperazinyl]-phenol monohydrochloride, methanol(1:1); mp. 178.0° C. (compound 1.13).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted twice with 4-methyl-2-pentanone
  3. dissolutionThe undissolved product was dissolved in 2-propanol
  4. washThis solution and the combined organic layers were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt was filtered off
  9. customcrystallized twice
  10. additionfirst from a mixture of 2-propanol and water (10:1 by volume)
  11. additionfrom a mixture of methanol and water (10:1 by volume)
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-b5c40ade53b249f490e64ba1819f6c24
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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