Hydrochloric Acid → HCID 10024995, compound

HRID 1609221Notes

Reaction equation

HRID 1609221 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)(C)(C)C.[Cl:10][C:11]1[CH:38]=[CH:37][C:14]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25]C)=[CH:22][CH:23]=3)[C:18]([S:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:17]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:13][CH:12]=1.Cl>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[C:18]([S:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[C:17]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6387tert-Butyl mercaptanHCID 6451240Aluminum(III) ChlorideHCID 20084251HCID 20084251, compound

Product 1

HCID 10024995HCID 10024995, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of anhydrous aluminum chloride (4.8 g, 36 mmol) in CH2Cl2 (15 ml) was added t-butyl mercaptan (12 ml) followed by ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindole-2-carboxylate (3.77 g; 11 mmol), prepared as in step 2, and the resulting mixture was stirred at 0° C. for 45 min. The reaction mixture was then poured into ice and aqueous 1N hydrochloric acid (100 ml) and extracted with ethyl acetate. The organic phase was concentrated in vacuo to provide 4.2 g of crude oily ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindole-2-carboxylate which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-ddd73005fec64d1c865ad7439ee86d2c
Source dataset
uspto-grants-1995_03
Patent number
US05399699

Reaction notes

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