HCID 22728130, compound → HCID 22728126, compound

HRID 2086161Notes

Reaction equation

HRID 2086161 reaction equation
[CH:1]1([NH:5][S:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:21]([Cl:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=3[Cl:26])[CH:12]=[CH:11][C:10]=2[OH:27])(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[NH2:23][C:19]1[CH:18]=[C:17]([Cl:26])[C:16]([O:15][C:13]2[CH:12]=[CH:11][C:10]([OH:27])=[C:9]([S:6]([NH:5][CH:1]3[CH2:4][CH2:3][CH2:2]3)(=[O:8])=[O:7])[CH:14]=2)=[C:21]([Cl:22])[CH:20]=1

Participants

5

Reactant 2

HCID 22728130HCID 22728130, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22728126HCID 22728126, compoundYield 128.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-Cyclobutyl-5-(2,6-dichloro-4-nitro-phenoxy)-2-hydroxy-benzenesulfonamide (403 mg, 0.73 mmol) in ethanol (10 mL) at room temperature was added 10% palladium on carbon (60 mg), and the resulting mixture was placed on Parr shaker for 3 hours under 50 psi. hydrogen gas at room temperature. The reaction solution was filtered through Celite®, and the filtrate was concentrated to afford the title compound (379 mg) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ8.32 (s, 1H), 7.07-7.04 (dd, 1H), 6.95 (m, 2H), 6.67 (s, 2H), 4.68 (d, 1H), 3.81-3.68 (m, 1H), 2.16-2.08 (m, 2H), 1.7-1.58 (m, 4H). MS (APCI−) Calc: 402.1, Found: 401.3 (M−1).

Workup

  1. customat room temperature
  2. filtrationThe reaction solution was filtered through Celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9ec46f4b5ec541b5952aa96ede7323a1
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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