Sodium Hydroxide → HCID 16123486, compound

HRID 555924Notes

Reaction equation

HRID 555924 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][C:19]=2[Cl:20])=[O:14])[CH:3]=1.[OH-].[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][C:19]=2[Cl:20])=[O:14])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57576651HCID 57576651, compound

Product 1

HCID 16123486HCID 16123486, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Methyl 4-chloro-2-(3-chlorothiophene-2-carboxamido)benzoate (90 mg, 0.27 mmol) was dissolved in 4 mL of dimethylacetamide. 1 M NaOH (1 mL) was added and the reaction was stirred at room temperature overnight. The product was precipitated by the addition of 1 M HCl to the reaction mixture. The product was filtered and dried under vacuum to give 69 mg of white solid. 1H NMR (400 MHz, d6-DMSO): 12.08 (s, 1H), 8.68 (d, 1H), 8.05 (d, 1H), 8.03 (d, 1H), 7.32 (dd, 1H), 7.28 (d, 1H); MS (EI) for C12H7Cl2NO3S: 316 (M+H).

Workup

  1. customThe product was precipitated by the addition of 1 M HCl to the reaction mixture
  2. filtrationThe product was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d9f61470dfe64aaba1ff403d05507bc3
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

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