Hydrochloric Acid → [3-(2-Methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466755Notes

Reaction equation

HRID 1466755 reaction equation
O=[C:2]([CH3:15])[CH2:3][S:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.[C:16]1([NH:22]N)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CC(O)(C)C>[CH3:15][C:2]1[NH:22][C:16]2[C:21]([C:3]=1[S:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 66765032[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid

Product 1

HCID 56840408[3-(2-Methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid (0.200 g, 1.12 mmol) was dissolved in t-BuOH (5 mL) then phenylhydrazine (121 μL, 1.232 mmol) was added followed by HCl (1.232 mL, 1.0M in ether). The reaction was heated to 70° C. for 1 hour then cooled and submitted to aqueous workup to afford the title compound.

Workup

  1. temperaturethen cooled

Sources & evidence

ORD record
ord-9c5fdd6e8d4947449349c1014b6df517
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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