Sodium Hydroxide → HCID 68278296, compound

HRID 931443Notes

Reaction equation

HRID 931443 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=3)[O:18][C:19]=2[CH3:20])(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278417HCID 68278417, compound

Product 1

HCID 68278296HCID 68278296, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 40 (355 mg, 0.82 mmol) and 2 M NaOH (10 mL) in dioxane (10 mL) gave acid 41 (329 mg, 96%) as a white solid: mp (H2O) 221-223° C.; 1H NMR δ 13.16 (br s, 1H, CO2H), 8.05 (d, J=8.4 Hz, 2H, H-2, H-6), 7.94 (d, J=8.4 Hz, 2H, H-3, H-5), 7.33 (dd, J=8.5, 2.0 Hz, 1H, H-6′), 7.26 (d, J=2.0 Hz, 1H, H-2′), 7.14 (d, J=8.5 Hz, 1H, H-5′), 4.63 (s, 2H, CH2SO2), 3.84 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 2.16 (s, 3H, CH3); MS m/z 418.6 (MH+, 100%). Anal. calcd for C20H19NO7S.½H2O: C, 56.33; H, 4.73; N, 3.29. Found: C, 56.02; H, 4.59; N, 3.36%.

Sources & evidence

ORD record
ord-921ca75f95924bc8a2abe49cfa2642ea
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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