Triethylamine → HCID 85858599, compound

HRID 1487117Notes

Reaction equation

HRID 1487117 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1N=[CH:17][N:16](C(N2C=NC=C2)=O)[CH:15]=1.Cl.CNC.CCN(CC)CC>C1COCC1>[CH3:15][N:16]([CH3:17])[C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 158763-Nitrophenylacetic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 85858599HCID 85858599, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-(3-nitrophenyl)acetic acid (0.2 g, 1.104 mmol) in THF (6 ml) was added CDI (0.269 g, 1.656 mmol). resulting mixture was heated at 50° C. for 1 hr, cooled to room temperature and then dimethyl amine hydrochloride (0.108 g, 1.325 mmol) and Et3N (0.15 ml, 1.104 mmol) were added sequentially. Resulting reaction mixture was stirred for 24 h at ambient temperature. Solvents were evaporated under vacuum. The residue was purified by flash chromatography to obtain N,N-dimethyl-2-(3-nitrophenyl)acetamide (0.192, 84% yield).

Workup

  1. customresulting mixture
  2. temperaturecooled to room temperature
  3. customResulting
  4. customreaction mixture
  5. customSolvents were evaporated under vacuum
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6e5f4d1505ac4dc4a9f4b2eeff4cb8a7
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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