N-Methyl-4-nitroaniline → 2-bromo-N-methyl-N-(4-nitrophenyl)acetamide

HRID 989401Notes

Reaction equation

HRID 989401 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Li+].[Li+].[Br:18][CH2:19][C:20](Br)=[O:21]>O1CCOCC1>[Br:18][CH2:19][C:20]([N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[CH3:1])=[O:21]

Participants

5

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 11125Lithium CarbonateHCID 61147Bromoacetyl bromide

Product 1

HCID 226683752-bromo-N-methyl-N-(4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

23.5 g (0.15 mol) of N-methyl-4-nitroaniline are dissolved in 400 ml of dioxane and combined with 22.2 g (0.3 mol) of lithium carbonate. Then 32.2 g (0.18 mol) of bromoacetylbromide are added dropwise in such a way that the internal temperature does not exceed 33° C. After 18 hours' stirring the reaction solution is evaporated down to 100 ml, combined with 500 ml of water and stirred for 1 hour. The precipitate formed is suction filtered, washed with water and dried. The crude product is stirred in 400 ml of ethyl acetate at 40° C. Then the insoluble matter is filtered off, the solution is evaporated down and the solid residue is triturated with ether.

Workup

  1. customdoes not exceed 33° C
  2. customis evaporated down to 100 ml
  3. stirringstirred for 1 hour
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customdried
  8. stirringThe crude product is stirred in 400 ml of ethyl acetate at 40° C
  9. filtrationThen the insoluble matter is filtered off
  10. customthe solution is evaporated down
  11. customthe solid residue is triturated with ether

Sources & evidence

ORD record
ord-bea18bee3b6d4a8f80a41c8184565167
Source dataset
uspto-grants-2003_10
Patent number
US06638965B2

Reaction notes

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