Diethyl Ether → HCID 86583880, compound

HRID 431089Notes

Reaction equation

HRID 431089 reaction equation
[CH3:1][N:2]([CH3:15])[CH:3]([CH3:14])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[N:11][CH:12]=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.[CH3:15][N:2]([CH3:1])[CH:3]([CH3:14])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 85789338HCID 85789338, compound

Product 1

HCID 86583880HCID 86583880, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 45A (67 mg, 0.29 nmnol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (32 mg, 0.30 mmol) and stirred for 5 minutes. Next, ethyl 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 45 as a white solid. mp 100-102° C.; MS (CI/NH3) m/e 229(M+H)+. 1H NMR (D2O, 300 MHz) δ: 1.39 (d, J=7 Hz, 3H), 2.08 (m, 1H), 2.34 (m, 1H), 2.41 (s, 3H), 2.8 (s, 6H), 3.70 (m, 1H), 4.15-4.32 (m, 2H), 7.38 (d, J=8 Hz, 2H), 7.42-7.51 (m, 2H), 7.69 (d, J=8 Hz, 2H), 8.06 (d, J=3 Hz, 1H). Analysis calculated for C11H17N2ClO.1C7H8O3S: C, 53.93; H, 6.24; N, 6.99; Found: C, 53.67; H, 6.24; N, 7.02.

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-d8e118bac13e4a25964d358593f6b4f9
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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