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

HRID 2236445Notes

Reaction equation

HRID 2236445 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.CCN(CC)CC.[Br:19][CH2:20][C:21](Br)=[O:22]>C(Cl)Cl>[Br:19][CH2:20][C:21]([N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)=[O:22]

Participants

5

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 226683752-bromo-N-methyl-N-(4-nitrophenyl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.00 g (13.2 mmol) of N-methyl-4-nitroaniline and 1.46 g (14.5 mmol) of Et3N in 20 mL of CH2Cl2 at O° C. under N2 is treated with a solution of 5.33 g (26.4 mmol) of bromoacetyl bromide in 4 mL of CH2Cl2. After 3.5 h, the reaction is poured into ice water and extracted with CH2Cl2. The extract is treated with Darco, dried (MgSO4) and evaporated. The residue is filtered through Magnesol (CHCl3), evaporated and dried in vacuo to give 3.57 g (100%) of yellow solid. 1H NMR (DMSO-d6) δ 8.27 (d, 2H, J=7.47 Hz), 7.66 (d, 2H, J=7.47 Hz), 4.06 (s, 2H), 3.28 (s, 3H); MS (ESI) m/z 273.0 (M+1).

Workup

  1. extractionextracted with CH2Cl2
  2. additionThe extract is treated with Darco
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. filtrationThe residue is filtered through Magnesol (CHCl3)
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7a1554b645bb4e9598859ba4ca16e6a7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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