Sodium Hydroxide → [5-Fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid

HRID 457956Notes

Reaction equation

HRID 457956 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[S:26])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[S:26])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:27])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12968796[5-Fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 9799153[5-Fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [5-Fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid ethyl ester (4.39 g, 11.2 mmol) in ethanol (40 mL) was treated with aq 2 N NaOH (11 mL, 22.4 mmol). After stirring for 4 h, the solution was concentrated in vacuo until most of the ethanol was removed, and the mixture was acidified to pH of 1 with 2 N HCl. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give [5-fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid (4.0 g, 98%) as an off-white solid: mp 147–150° C.; Rf 0.27 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 13.23 (s, 1 H), 10.79 (t, J=5.7 Hz, 1 H), 8.23 (t, J=1.8 Hz, 1 H), 8.11 (ddd, J1=8.3 Hz, J2=2.7 Hz, J3=1.2 Hz, 1 H), 7.85 (br d, J=7.5 Hz, 1 H), 7.73 (dd, J, =8.9 Hz, J2=7.1 Hz, 1 H), 7.63 (t, J=8.1 Hz, 1 H), 7.03 (dd, J1=11.4 Hz, J2=2.4 Hz, 1 H), 6.86 (dt, J1=8.4 Hz, J2=2.4 Hz, 1 H), 5.07 (d, J=5.7 Hz, 2 H), 4.83 (s, 2 H). ESI-LC/MS m/z calcd for CO6 H13FN2O5S: 364.4. Found 363.0 (M−1)−. Anal. calcd for C16H13FN2O5S: C, 52.74: H, 3.60; N, 7.69. Found C, 52.65; H, 3.62; N, 7.58.

Workup

  1. concentrationthe solution was concentrated in vacuo until most of the ethanol
  2. customwas removed
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b17195ecb44842d9803f6c039a9baac8
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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