Sodium Hydroxide → HCID 68942493, compound

HRID 2180917Notes

Reaction equation

HRID 2180917 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:9])[CH:5]=[CH:4][C:3]=1[S:10][C:11]1[C:12](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([O:15]C)=[O:14].[OH-].[Na+]>C1COCC1.CO>[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:9])[CH:5]=[CH:4][C:3]=1[S:10][C:11]1[C:12](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68947259HCID 68947259, compound

Product 1

HCID 68942493HCID 68942493, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.16 g Methyl S-(2-amino-4-chloromethylphenyl)thiosalicylate was dissolved in THF (50 mL) and methanol (50 mL), and treated with 5N sodium hydroxide solution (20 mL) with stirring at room temperature for 17 h. The reaction mixture was concentrated in vacuo, diluted with water, and acidified to pH 1-2 with 6N hydrochloric acid. The resulting suspension was filtered, and recrystallized from n-heptane to provide S-(2-amino-4-chloromethylphenyl)thiosalicylic acid as a light gray solid, 1H NMR (300 MHz, CDCl3), δ 6.77 (dd, 1H, J=2.7 Hz, J=2.1 Hz), 6.83 (d, 1H, J=2.1 Hz), 7.18 (t, 1H), 7.367 (s, 1H), 7.32 (t, 1H), 7.38 (d, 1H, J=8.4 Hz), 8.13 (d, 1H, J=1.8 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. filtrationThe resulting suspension was filtered
  4. customrecrystallized from n-heptane

Sources & evidence

ORD record
ord-8b12d89631ea45eeb0561210a4c7c1f3
Source dataset
uspto-grants-2005_05
Patent number
US06890919B2

Reaction notes

Loading…