Triethylamine → HCID 86610167, compound

HRID 1510153Notes

Reaction equation

HRID 1510153 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.Cl[C:20]([CH3:24])([CH3:23])[C:21]#[CH:22]>O.C1COCC1.[Cu]>[CH3:23][C:20]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])([CH3:24])[C:21]#[CH:22]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 86610167HCID 86610167, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl anthranilate (5.54 g, 36.6 mmol), triethylamine (3.48 g, 34.5 mmol), cuprous chloride (0.21 g, 2.15 mmol), copper powder (0.163 g, 2.56 mmol) in H2O (4 mL) and THF (14 mL) was added 3-chloro-3-methyl-1-butyne (2.21 g, 21.6 mmol). After heating to 65° C. for 4 h the reaction was cooled, diluted with water and extracted using diethyl ether (three times). The combined organic layers were washed with water, dried using MgSO4 and concentrated under vacuum. Purification by silica gel chromatography (5% EtOAc/hexanes-10% EtOAc/hexanes) afforded the desired product.

Workup

  1. temperaturewas cooled
  2. extractionextracted
  3. washThe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customPurification by silica gel chromatography (5% EtOAc/hexanes-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ee55188cf8ca48b9800abf35feb909ce
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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