Sodium Hydroxide → HCID 68278589, compound

HRID 931447Notes

Reaction equation

HRID 931447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=3)[O:15][C:16]=2[CH3:17])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278316HCID 68278316, compound

Product 1

HCID 68278589HCID 68278589, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 46 (491 mg, 1.26 mmol) and 1 M NaOH (10 mL) in dioxane (10 mL) gave acid 47 (354 mg, 75%) as a white solid: mp (H2O) 269-272° C.; 1H NMR δ 13.20 (br s, 1H, CO2H), 8.05 (d, J=8.5 Hz, 2H, H-2, H-6), 7.91 (d, J=8.5 Hz, 2H, H-3, H-5), 7.84-7.89 (m, 2H, H-2′, H-6′), 7.47 (br t, J=8.8 Hz, 2H, H-3′, H-5′), 4.74 (s, 2H, CH2SO2), 2.06 (s, 3H, CH3); MS m/z 376.5 (MH+, 100%). Anal. calcd for C18H14FNO5S.¼H2O: C, 56.91; H, 3.85; N, 3.69. Found: C, 57.15; H, 3.63; N, 3.59%.

Sources & evidence

ORD record
ord-74b9001e720a46f4a4c321c903b35f93
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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