3-Ethylaniline → HCID 51356953, compound

HRID 1623761Notes

Reaction equation

HRID 1623761 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:31]([C:33]1[CH:34]=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=1)[CH3:32]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH2:31][CH3:32])[CH:34]=1)=[O:9]

Participants

5

Reactant 3

HCID 114753-EthylanilineHCID 682631,1'-CarbonyldiimidazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 51356953HCID 51356953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method B; 200 mg, 0.65 mmol) was added to a stirred suspension of CDI (106 mg, 0.65 mmol) in THF (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and 3-ethylbenzenamine (79 mg, 0.65 mmol) was added dropwise. After refluxing for 14 h, the reaction mixture was concentrated to obtain crude product. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (10:1) to yield the title compound. 80 mg.

Workup

  1. temperatureAfter refluxing for 14 h
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain crude product
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-65e04e08a5374166ae33ce0d2ca01bf5
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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