Hydrochloric Acid → HCID 68679776, compound

HRID 2240066Notes

Reaction equation

HRID 2240066 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13].Cl[CH2:16][S:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18].CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 114244631-(3-Chloro-propoxy)-2-nitro-benzeneHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68679776HCID 68679776, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(3-chloro-propoxy)-2-nitrobenzene (1.2 g, 6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (2.16 g, 9 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 (18 mL, 18 mmoles) over a half 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 recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (1.9 g, 4.5 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 recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-634b985c13bb46c78913c1bad992faf2
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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