Triethylamine → Ammonium Hydroxide

HRID 1042714Notes

Reaction equation

HRID 1042714 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25]>CN(C1C=CN=CC=1)C.C1COCC1>[NH4+:11].[OH-:12].[Br:22][CH2:23][C:24]([NH:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])=[O:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 8261032-Tert-butyl-5-nitroaniline

Product 2

HCID 14923Ammonium HydroxideHCID 219613852-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-tert-Butyl-5-nitrobenzenamine (70 g, 359 mmol) and a catalytic amount of DMAP were dissolved into THF (1.5 L) under N2. Triethylamine (109 g, 1077 mmol) was added and the solution was cooled to 0° C. Bromoacetyl bromide (207 g, 1023 mmol) was then added and the reaction was stirred at room temperature for 16 hours. The reaction was then partially concentrated under reduced pressure, treated with water, and extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4 and concentrated to a black oil. The oil was purified using silica chromatography, 95:5:0.5 CH2Cl2:MeOH:NH4OH, giving 2-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide as a brown solid.

Workup

  1. concentrationThe reaction was then partially concentrated under reduced pressure
  2. additiontreated with water
  3. extractionextracted three times with EtOAc
  4. washThe EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a black oil
  7. customThe oil was purified

Sources & evidence

ORD record
ord-b5b30d1eeae0461cbee1c135b7a329d5
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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