Triethylamine → HCID 178426651, compound

HRID 237666Notes

Reaction equation

HRID 237666 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:11].Cl.[NH2:13][OH:14].C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:6]([NH:13][OH:14])=[NH:7])=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 110850704-Bromo-3,5-dimethyl-benzonitrile

Product 1

HCID 178426651HCID 178426651, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-3,5-dimethyl-benzonitrile (1.50 g), hydroxylamine hydrochloride (0.90 g), triethylamine (1.8 mL) and ethanol (30 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the mixture is concentrated, the residue is taken up in water, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 7:3→3:7) to give the title compound. LC (method 11): tR=0.73 min; Mass spectrum (ESI+): m/z=243/245 (Br) [M+H]+.

Workup

  1. temperatureat reflux temperature for 4 h
  2. concentrationthe mixture is concentrated
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. extractionThe combined extract
  5. washis washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 7:3→3:7)

Sources & evidence

ORD record
ord-fe2b26db05e3496a8c9f94e8def1af03
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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