Triethylamine → HCID 22728152, compound

HRID 2086159Notes

Reaction equation

HRID 2086159 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.C(N(CC)CC)C.[CH:32]1([NH2:36])[CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[CH:32]1([NH:36][S:11]([C:9]2[CH:10]=[C:5]([O:4][C:3]3[C:2]([Cl:1])=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:17]=3[Cl:24])[CH:6]=[CH:7][C:8]=2[O:15][CH3:16])(=[O:13])=[O:12])[CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75645CyclobutylamineHCID 155414425-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride

Product 1

HCID 22728152HCID 22728152, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride (1.3 grams, 3.2 mmol) in methylene chloride (30 mL) at 0° C. was added triethylamine (0.58 mL, 4.1 mmol) followed by cyclobutylamine (0.27 mL, 3.2 mmol). After stirring at room temperature for 2 hours, the reaction mixture was quenched with 1N hydrochloric acid (25 mL) and extracted with methylene chloride (3 times 15 mL). The combined organic extracts were washed with 1N HCl (20 mL), saturated aqueous NaHCO3 (2 times 20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (30% ethyl acetate in hexane) to afford the title compound (531 mg). 1H NMR (400 MHz, CDCl3) δ8.28 (s, 2H), 7.28 (d, 1H), 7.07-7.04 (dd, 1H), 6.98 (d, 1H), 5.26 (d, 1H), 3.96 (s, 3H), 3.71-3.69 (m, 1H), 1.99-1.92 (m, 2H), 1.74-1.68 (m, 2H), 1.57-1.48 (m, 2H). MS (APCI−) Calc: 446.1, Found: 445.2 (M−1).

Workup

  1. customthe reaction mixture was quenched with 1N hydrochloric acid (25 mL)
  2. extractionextracted with methylene chloride (3 times 15 mL)
  3. washThe combined organic extracts were washed with 1N HCl (20 mL), saturated aqueous NaHCO3 (2 times 20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-47db5ef08a084a78a0a98479afd455cc
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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