Chloride → HCID 19603795, compound

HRID 1604657Notes

Reaction equation

HRID 1604657 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][C:31]([O:33]CC2C=CC=CC=2)=[O:32])=[CH:22]1.[OH-].[Na+].[Cl-].Cl>ClCCl.O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([CH2:30][C:31]([OH:33])=[O:32])=[CH:22]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19603727HCID 19603727, compoundHCID 19603827Benzyl (1H-indol-3-yl)acetate

Product 1

HCID 19603795HCID 19603795, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (0.30 g), benzyl indole-3-acetate (0.25 g), sodium hydroxide (0.24 g) and small amount of cetyl trymethylammonium chloride in dichloromethane (10 ml) was stirred under reflux for 3 hours. After water was added to the reaction mixture, the mixture was neutralized with diluted hydrochloric acid and the resulting mixture was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of dichloromethane and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indole-3-acetic acid (0.18 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. washeluted with a mixture of dichloromethane and methanol
  4. additionThe fractions containing the objective compound
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8b0191c799741488e3ce653ecaaf150
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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