Benzoyl chloride → HCID 54175923, compound

HRID 326098Notes

Reaction equation

HRID 326098 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH2:16][CH2:17][NH2:18])[CH3:2].[OH-].[Na+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH2:16][CH2:17][NH:18][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 53912912HCID 53912912, compound

Product 1

HCID 54175923HCID 54175923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

61.7 g (0.223 mol) of the 2-aminoethyl-5-fluoro-indole-3-acetic acid ethyl ester produced in (d) are dissolved in 600 ml of methylene chloride and the solution is covered with a layer of 150 ml of 2 N sodium hydroxide solution. A solution of 43 g (0.245 mol) of benzoyl chloride is added, at 0°-5°, in the course of 21/2 hours, while stirring vigorously, and extraction by stirring is then carried out for a further hour. The methylene chloride phase is then separated off, washed with water, dried over MgSO4 and concentrated to dryness by evaporation. The residue crystallises on being taken up in ether, to form colourless crystals of 2-[(benzoyl-amino)-ethyl]-5-fluoro-indole-3-acetic acid ethyl ester.

Workup

  1. extractionextraction
  2. stirringby stirring
  3. waitis then carried out for a further hour
  4. customThe methylene chloride phase is then separated off
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness by evaporation
  8. customThe residue crystallises

Sources & evidence

ORD record
ord-9273c0a04331433eadc8a93cabcb5144
Source dataset
uspto-grants-1984_04
Patent number
US04444768

Reaction notes

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