Potassium Hydroxide → HCID 44549142, compound

HRID 2238436Notes

Reaction equation

HRID 2238436 reaction equation
[OH-].[K+].[CH2:3]([N:10]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[S:11]([C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([C:24]([O:26]C)=[O:25])=[CH:21]2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O.C(Cl)Cl>[CH2:28]([N:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[S:11]([C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([C:24]([OH:26])=[O:25])=[CH:21]2)=[CH:16][CH:15]=1)(=[O:12])=[O:13])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 44549141HCID 44549141, compound

Product 1

HCID 44549142HCID 44549142, compoundYield 108.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of KOH (720 mg, 12.8 mmol) in MeOH (5 mL) and H2O (2 mL) was added dropwise to a solution of 209 (1.90 g, 4.27 mmol) in MeOH (10 mL) and CH2Cl2 (15 mL). After 48 h at room temperature CH2Cl2 and H2O were added. The aqueous layer was separated and acidified to pH 2 with 2 M HCl. The resulting white precipitate was collected, dissolved in CH2Cl2, and the solution was washed with H2O and brine. The CH2Cl2 layer was dried, the solvent was evaporated, and the residue was dried in a vacuum desiccator. Recrystallization from CH2Cl2/petroleum ether gave 7-[(dibenzylamino)sulfonyl]-2-naphthoic acid (210) (2.00 g, 99%) as colorless crystals: mp 189-190° C.; 1H NMR (CDCl3) 8 (CO2H not observed) 8.76 (s, 1H), 8.47 (s, 1H), 8.29 (dd, J=8.6, 1.5 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.92 (dd, J=8.7, 1.8 Hz, 1H), 7.23-7.15 (m, 6H), 7.12-7.05 (m, 4H), 5.29 (s, 1H), 4.42 (s, 4H); 13C NMR δ 170.8, 139.0, 137.0, 135.4, 133.1, 131.4, 129.7, 129.3, 128.6, 128.5, 128.4, 128.2, 128.1, 127.8, 125.3, 50.7. Anal. (C25H21NO4S) C, H, N.

Workup

  1. customThe aqueous layer was separated
  2. customThe resulting white precipitate was collected
  3. dissolutiondissolved in CH2Cl2
  4. washthe solution was washed with H2O and brine
  5. dry with materialThe CH2Cl2 layer was dried
  6. customthe solvent was evaporated
  7. customthe residue was dried in a vacuum desiccator
  8. customRecrystallization from CH2Cl2/petroleum ether

Sources & evidence

ORD record
ord-b489df451d704e20a1e694ffa81e9f55
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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