4-Chlorobenzoyl chloride → HCID 53916289, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[CH2:17][CH2:18][NH2:19])[CH3:2].[OH-].[Na+].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[CH2:17][CH2:18][NH:19][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([Cl:23])=[CH:25][CH:26]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
61.7 g (0.223 mol) of the 2-aminoethyl-5-methoxy-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 p-chlorobenzoyl 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-[(p-chlorobenzoyl-amino)-ethyl]-5-methoxy-indole-3-acetic acid ethyl ester having a melting point of 136°-138°.
Workup
- extractionextraction
- stirringby stirring
- waitis then carried out for a further hour
- customThe methylene chloride phase is then separated off
- washwashed with water
- dry with materialdried over MgSO4
- concentrationconcentrated to dryness by evaporation
- customThe residue crystallises
Sources & evidence
- ORD record
- ord-7d731dc529cb43c3b7cc4b6ca198f86b
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04444768
Reaction notes
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