Water → Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-methoxy-1H-indol-2-yl)-2,2-dimethylpropanoate

HRID 1975732Notes

Reaction equation

HRID 1975732 reaction equation
Cl.[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[C:25]([S:29][CH2:30][C:31](=O)[CH2:32][C:33]([CH3:40])([CH3:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH3:28])([CH3:27])[CH3:26].O>C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:30]([S:29][C:25]([CH3:28])([CH3:26])[CH3:27])=[C:31]2[CH2:32][C:33]([CH3:39])([CH3:40])[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 3576811Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoateHCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Product 1

HCID 19935666Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-methoxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride (50 g; 190 mmol), prepared as in step 1, was dissolved in 400 mL toluene and 220 mL acetic acid. Sodium acetate (17.1 g; 210 mmol) was added followed by the addition of ethyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (49 g; 188 mmol), prepared as in step 2. The reaction was stirred in the dark at room temperature for 4 days. The mixture was poured into water and extracted with ethyl acetate. The combined extracts were washed with water. Solid sodium bicarbonate was added to the organic extracts and the mixture was filtered. The filtrate was washed with water and brine, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was taken up in hot ethyl acetate and filtered. The solvent was removed and the product was recrystallized from pentane to give ethyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropionate as a fluffy white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. additionSolid sodium bicarbonate was added to the organic extracts
  4. filtrationthe mixture was filtered
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe product was recrystallized from pentane

Sources & evidence

ORD record
ord-eae8696765dd4cf5bb3ec3f166ff16eb
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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