Sodium Hydroxide → HCID 18468137, compound

HRID 2229583Notes

Reaction equation

HRID 2229583 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[S:29])[NH:15][CH2:16][C:17]1[S:18][C:19]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([F:28])[C:20]=2[N:21]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[S:29])[NH:15][CH2:16][C:17]2[S:18][C:19]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([F:28])[C:20]=3[N:21]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:30])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22093487HCID 22093487, compound

Product 1

HCID 18468137HCID 18468137, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid ethyl ester (2.0 g, 4.3 mmol) in ethanol (22 mL) and treated with aq 2 N NaOH (13 mL, 26 mmol). After stirring for 2 h, the solution was concentrated in vacuo to remove most of the ethanol and acidified to pH 1 with aq 2 N HCl. The product was extracted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to give {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid as an orange solid (1.05 g, 57%): mp 150° C.; Rf 0.50 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 13.76 (br s, 1H), 7.83 (br t, J=8.0 Hz, 1H), 7.79-7.70 (m, 1H), 7.14 (dd, J1=11.1 Hz, J2=2.4 Hz, 1H), 6.84 (dt, J1=8.4 Hz, J2=2.4 Hz, 1H), 5.37 (d, J=5.7 Hz, 2H), 4.58 (s, 2H). ESI-LC/MS m/z calcd for C17H10F4N2O3S2: 430.4; Found 429.0 (M−1)−. Anal. calcd for C17H10F4N2O3S2: C, 47.44; H, 2.34; N, 6.51; S, 14.90. Found C, 46.72; H, 2.81; N, 5.85; S, 12.02. Ethanol and water may still have been in the sample for the analytical values to be off.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customto remove most of the ethanol
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with saturated NaCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-68d11fb66b174a7da7b645eef7683c7e
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

Loading…