Sodium Hydroxide → HCID 68278368, compound

HRID 931434Notes

Reaction equation

HRID 931434 reaction equation
[Br: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>[Br: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 68278496HCID 68278496, compound

Product 1

HCID 68278368HCID 68278368, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 28 (320 mg, 0.71 mmol) and 2 M NaOH (10 mL) in dioxane (10 mL) gave acid 29 (216 mg, 70%) as a white solid: mp (DCM)>310° C.; 1H NMR δ 13.15 (br s, 1H, CO2H), 7.93 (br d, J=8.3 Hz, 2H, H-2, H-6), 7.84 (ddd, J=8.6, 2.3, 1.7 Hz, 2H, H-2′, H-6′), 7.68-7.73 (m, 4H, H-3, H-5, H-3′, H-5′), 4.70 (s, 2H, CH2SO2), 2.19 (s, 3H, CH3); MS m/z 437.0 (MH+, 100%), 439.0 (MH+, 100%). Anal. calcd for C18H14BrNO5S.½CH2Cl2: C, 47.08; H, 3.12; N, 2.89. Found: C, 47.09; H, 2.80; N, 2.99%.

Sources & evidence

ORD record
ord-4fe5812dbf964e1a9a2ec617ae0d85a8
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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