Triethylamine → HCID 22349419, compound

HRID 896019Notes

Reaction equation

HRID 896019 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:19]Br.[CH2:22]([O:24][CH2:25][CH2:26][NH2:27])[CH3:23].C(N(CC)CC)C>C(O)C>[CH2:22]([O:24][CH2:25][CH2:26][N:27]1[CH2:19][C:5]2[C:4](=[CH:9][CH:8]=[C:7]([O:10][C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[CH:6]=2)[C:3]1=[O:21])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66970EthoxyethylamineHCID 69694189HCID 69694189, compound

Product 1

HCID 22349419HCID 22349419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-Bromomethyl-4-(4-methoxy-phenoxy)-benzoic acid methyl ester (0.2 grams, 0.57 mmol) and 3 mL of ethanol was added ethoxyethylamine (0.073 mL, 0.062 grams, 0.70 mmol) and triethylamine (0.098 mL, 0.071 grams, 0.7 mmol). After shaking for 4 hours at 50° C., the mixture was cooled to room temperature and concentrated under a stream of nitrogen. The residue was treated with methanesulfonic acid (3 mL) and methionine (0.13 grams). The mixture was shaken for 24 hours at room temperature and was then heated to 50° C. for 6 hours. After cooling to room temperature, the mixture was poured into aqueous 5 M sodium hydroxide with cooling in an ice bath, and the pH was adjusted to 8 with aqueous sodium bicarbonate. The aqueous phase was extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification by radial chromatography (2 mm silica gel plate) eluting with 3% methanol-methylene chloride afforded 30 miligrams of 2-(2-Ethoxy-ethyl)-5-(4-hydroxy-phenoxy)-2,3-dihydro-isoindol-1-one as a colorless syrup. MS: 314.3 [M+H]+

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationconcentrated under a stream of nitrogen
  3. additionThe residue was treated with methanesulfonic acid (3 mL) and methionine (0.13 grams)
  4. stirringThe mixture was shaken for 24 hours at room temperature
  5. temperaturewas then heated to 50° C. for 6 hours
  6. temperatureAfter cooling to room temperature
  7. additionthe mixture was poured into aqueous 5 M sodium hydroxide
  8. temperaturewith cooling in an ice bath
  9. extractionThe aqueous phase was extracted 3 times with ethyl acetate
  10. dry with materialthe combined organic layers were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customPurification by radial chromatography (2 mm silica gel plate)
  14. washeluting with 3% methanol-methylene chloride

Sources & evidence

ORD record
ord-a1c8062cb8db4daca91a19780070397e
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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