2,4,5-Trichloronitrobenzene → 3-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanol

HRID 2420292Notes

Reaction equation

HRID 2420292 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](Cl)=[CH:4][C:3]=1[Cl:12].[NH2:13][CH2:14][CH2:15][CH2:16][OH:17].[K]>C(O)CCC>[Cl:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 69832,4,5-TrichloronitrobenzeneHCID 90863-Amino-1-propanolHCID 5462222Potassium

Product 1

HCID 1129553-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 113.2 parts of 1,2,4-trichloro-5-nitrobenzene, 75 parts of 3-amino-1-propanol, 0.2 parts of potassium iodic and 200 parts of butanol is stirred and refluxed overnight. The butanol is removed be evaporated in vacuo and water is added to the residue. The product is extracted with 4-methyl-2-pentanone. The extract is washed a few times with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichoromethane and 5% of methanol as elluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and crystallized from a mixture of 2,2'-oxybispropane and 2-propanol, yielding 31.7 parts of 3-[(4,5-dichloro-2-nitrophenyl)amino]-1-propanol; mp. 97° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe butanol is removed
  3. custombe evaporated in vacuo and water
  4. additionis added to the residue
  5. extractionThe product is extracted with 4-methyl-2-pentanone
  6. washThe extract is washed a few times with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichoromethane and 5% of methanol as elluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. customThe residue is triturated in 2,2'-oxybispropane
  15. filtrationThe product is filtered off
  16. customcrystallized from a mixture of 2,2'-oxybispropane and 2-propanol

Sources & evidence

ORD record
ord-9373bc7db1ea40c2892ae46e72ed3ade
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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