Sodium Hydroxide → HCID 2829056, compound

HRID 453611Notes

Reaction equation

HRID 453611 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:9]=[C:8]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[S:7][C:6]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C1COCC1.O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([C:8]2[S:7][C:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:5]([CH2:4][C:3]([OH:25])=[O:2])[CH:9]=2)=[O:18])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68494851HCID 68494851, compound

Product 1

HCID 2829056HCID 2829056, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.15 g (0.40 mmol) of the above ester in a mixture of 2 mL of THF and 1 mL of H2O was added 0.60 mL (0.60 mmol) of 1 N NaOH at room temperature. The resulting mixture was refluxed for 3 h. The solvent was evaporated in vacuo. The residue was dissolved in 5 mL of H2O and acidified with 0.11 mL of 1N HCl to give 0.14 g (100%) of 1 as a pale yellow solid: mp 142-143° C.; 1H NMR (400 MHz, CDCl3) δ 9.75 (brs, 1H), 7.84 (d, J=8.6 Hz, 2H), 7.62 (s, 1H), 7.462 (d, J=8.6 Hz, 2H), 7.46 (m, 5H), 3.71 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 186.6, 176.5, 150.6, 140.9, 138.8, 137.2, 136.1, 132.4, 130.6, 129.7, 129.3, 129.2, 129.1, 128.9, 34.0; IR (KBr) cm−1 3058, 2921, 1715, 1628; LREIMS C19H13ClO3S requires 356.03. Found: 355 ([M+], 100%), 310 (25%), 244 (25%), 139 (42%).

Workup

  1. temperatureThe resulting mixture was refluxed for 3 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in 5 mL of H2O

Sources & evidence

ORD record
ord-e148677a9c474c7bb30527bb0715962e
Source dataset
uspto-grants-2013_07
Patent number
US08492428B2

Reaction notes

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