Triethylamine → HCID 54534971, compound

HRID 1084323Notes

Reaction equation

HRID 1084323 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[CH2:20][C:21]([OH:23])=[O:22])([O-:12])=[O:11].C(N(CC)CC)C>C(OC(=O)C)(=O)C>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[C:20](=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[C:21]([OH:23])=[O:22])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 14740976(5-Methyl-2-nitrophenyl)acetic acid

Product 1

HCID 54534971HCID 54534971, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-bromobenzaldehyde (19.5 g, 106 mmol) and 2-nitro-5-methyl-phenylacetic acid (20.6 g, 106 mmol; J. G. Atkinson et. al., Tetrahedron Lett., 2857, 1979) in 100 ml of acetic anhydride was added triethylamine (14.7 ml, 106 mmol) and the resulting reddish solution was heated at 40° C. for 70 hours. Most of the acetic anhydride was evaporated under vacuum and the residue was diluted with ethyl acetate and washed with sat. NH4Cl, H2O, and brine. Drying (MgSO4) and evaporation yielded 37.87 g (99%) of product as a yellow solid which was used in the next reaction without purification.

Workup

  1. customMost of the acetic anhydride was evaporated under vacuum
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with sat. NH4Cl, H2O, and brine
  4. customDrying
  5. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-52eca77d958d4a6fa3ac3c11ebaf4265
Source dataset
uspto-grants-1991_04
Patent number
US05004740

Reaction notes

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