Diethyl Ether → HCID 20607401, compound

HRID 431086Notes

Reaction equation

HRID 431086 reaction equation
[CH3:1][N:2]([CH3:15])[C@H:3]([CH3:14])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([Br:13])[C:9]([Cl:12])=[N:10][CH:11]=1.O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(OCC)C>C(OCC)(=O)C>[C:17]1([CH3:27])[CH:18]=[CH:19][C:20]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1.[CH3:1][N:2]([CH3:15])[C@H:3]([CH3:14])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([Br:13])[C:9]([Cl:12])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 9814622HCID 9814622, compound

Product 1

HCID 20607401HCID 20607401, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 33A (102 mg, 0.349 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (73 mg, 0.384 mmol) and stirred for 5 minutes. Then diethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. The residue was then dried under vacuum to provide 33 as a white hygroscopic solid. MS (CI/NH3) m/e 293 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.38 (s, 3H), 2.91 (d, J=37 Hz, 6H), 3.90 (m, 1H), 4.26 (dd, J=8, 12 Hz, 1H), 4.38 (dd, J=4, 12 Hz, 1H), 7.34 (d, J=8 Hz, 2H), 7.67 (d, J=8 Hz, 2H), 7.84 (d, J=3 Hz, 1H), 8.08 (d, J=3 Hz, 1H); Analysis calculated for C10H14N2BrClO.1.1C7H8O3S.0.2H2O: C, 43.69; H, 4.81; N, 5.76; Found: C, 43.66; H, 4.62; N, 5.47; [α]25D=−0.87° (c=0.69, MeOH).

Workup

  1. stirringstirred for an additional 5 minutes
  2. customThe ether was decanted
  3. customThe residue was then dried under vacuum

Sources & evidence

ORD record
ord-236bb965b9504548b3f93771d3363aa4
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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