Hydrochloric Acid → HCID 69059583, compound

HRID 734831Notes

Reaction equation

HRID 734831 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:30]=[CH:29][C:21]4[S:22][C:23]([C:25]([O:27]C)=[O:26])=[CH:24][C:20]=4[CH:19]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.Cl>CCO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:30]=[CH:29][C:21]4[S:22][C:23]([C:25]([OH:27])=[O:26])=[CH:24][C:20]=4[CH:19]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69058356HCID 69058356, compound

Product 1

HCID 69059583HCID 69059583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

22.3 mL of 1N NaOH was added to a suspension of 3.0 g (7.43 mmol) of methyl 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]benzo[b]thiophen-2-carboxylate in 100 mL of EtOH and the reaction mixture was stirred overnight at RT. The reaction solution was cooled to 0° C. and adjusted to pH 6 by the dropwise addition of 1N HCl. The precipitated product was filtered off, washed with EtOH, and dried in the air. As the product still contained educt, the hydrolysis described above was repeated. Yield: 2.7 g (93% of theoretical); C22Hl2ClNO2S (M=389.855); calc.: molpeak (M+H)+: 390/392 (Cl); found: molpeak (M+H)+: 390/392 (Cl); Rf value: 0.89 (silica gel, PE/EtOAc 1:1).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. filtrationThe precipitated product was filtered off
  3. washwashed with EtOH
  4. customdried in the air

Sources & evidence

ORD record
ord-2731306a1dc645f8833aca13ec726c3f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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