HCID 735094, compound → HCID 730263, compound

HRID 1599527Notes

Reaction equation

HRID 1599527 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20]C)=[O:19])(=[O:13])=[O:12]>[OH-].[Na+]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([OH:20])=[O:19])(=[O:13])=[O:12]

Participants

3

Reactant 1

HCID 735094HCID 735094, compound

Product 1

HCID 730263HCID 730263, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 10.8 g (31.7 mmol) of methyl 3-((2-naphthalenyl)sulfonyl)aminobenzoate (12) as prepared in Example 2 in 100 mL of 1N NaOH was stirred at 50° C. for 20 min. The reaction mixture was quenched with excess 2N HCl, diluted with tetrahydrofuran to dissolve the suspension. Ether was added to induce phase separation. The organic extract was dried (MgSO4) and the solvent removed in vacuo. Trituration from ether/tetrahydrofuran/hexane gave 10.0 g of the title compound: 1H-NMR (200 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.13 (t, 2H), 7.99 (d, 1H), 7.54-781 (m, 5H), and 7.77-7.43 ppm (m, 2H). Mass spectrum (MALDI-TOF) calcd. for C17H13NO4S: 328.1 (M+H) and 350.0 (M+Na). Found: 328.7 (M+H), 349.8 (M+Na).

Workup

  1. customThe reaction mixture was quenched with excess 2N HCl
  2. additiondiluted with tetrahydrofuran
  3. dissolutionto dissolve the suspension
  4. additionEther was added
  5. customphase separation
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9a787470213e48dfa6ee642739acd6b0
Source dataset
uspto-grants-1998_04
Patent number
US05741819

Reaction notes

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