Water → HCID 68512351, compound

HRID 1929336Notes

Reaction equation

HRID 1929336 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].Br[CH2:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23].O>CN(C)C=O>[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[CH2:15][O:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:3])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 68512351HCID 68512351, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

add 561 mg of anhydrous potassium hydroxide to a solution of 1.54 g of 4-amino-3-nitrophenol in 6 cm3 of N,N-dimethylformamide. Add dropwise, to the purple solution obtained, 2.4 g of 2-(bromomethyl)-1,3-dichlorobenzene in solution in 2 cm3 of N,N-dimethylformamide, without exceeding 20° C. After stirring the reaction mixture for about twenty hours at a temperature around 20° C., the reaction mixture is poured into 200 cm3 of water. The mixture obtained is extracted three times with 100 cm3 of ethyl acetate. The combined organic phases are washed five times with 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated under reduced pressure (0.2 kPa). The residue is taken up successively in a 50/50 mixture of diethyl oxide and diisopropyl oxide, and finally drained, washed three times with 2 cm3 of diisopropyl oxide, then dried under reduced pressure in the presence of potassium hydroxide. We obtain 2.4 g of 4-[(2,6-dichlorobenzyl)oxy]-2-nitroaniline in the form of a white powder, which has the following characteristics:

Workup

  1. additionAdd dropwise, to the purple solution
  2. customobtained
  3. customwithout exceeding 20° C
  4. customThe mixture obtained
  5. extractionis extracted three times with 100 cm3 of ethyl acetate
  6. washThe combined organic phases are washed five times with 50 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (0.2 kPa)
  10. additionThe residue is taken up successively in a 50/50 mixture of diethyl oxide and diisopropyl oxide
  11. washwashed three times with 2 cm3 of diisopropyl oxide
  12. dry with materialdried under reduced pressure in the presence of potassium hydroxide

Sources & evidence

ORD record
ord-04ad11161e2a4d63bd6754347d9525be
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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