Hydrochloric Acid → HCID 58812147, compound

HRID 2240074Notes

Reaction equation

HRID 2240074 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.Cl[CH2:15][S:16]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17].CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:15][S:16]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:18].[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:15][S:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 43044241-(2-chloroethoxy)-3-nitrobenzeneHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxide

Product 2

HCID 58812147HCID 58812147, compoundHCID 68680105HCID 68680105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-chloro-ethoxy)-3-nitrobenzene (1.12 g, 5.6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (1.6 g, 6.72 mmoles) was stirred in THF (50 mL) at −78° C., in a round bottom flask under nitrogen. A solution of 1M potassium t-butoxide was added dropwise (16.8 mL, 16.8 mmoles) over a half an hour period. Temperature was allowed to rise to −40° C., and the reaction mixture was stirred at this temperature for 5 hours. The reaction mixture was poured into cold 2N HCl, extracted with EtOAc, dried over Na2SO4, and concentrated under vacuum. Compound was purified by normal phase HPLC using as eluent 40% EtOAc/hexane to afford the title compound as an off-white solid (0.9 g, 2.24 mmoles), and 1-[4-(2-chloro-ethoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene (0.79 g, 2.1 mmoles).

Workup

  1. customto rise to −40° C.
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customCompound was purified by normal phase HPLC

Sources & evidence

ORD record
ord-19587b909d9f490abf79bdcc71f47c87
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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