Diethyl Ether → HCID 20607402, compound

HRID 431087Notes

Reaction equation

HRID 431087 reaction equation
[CH3:1][N:2]([CH3:15])[C@H:3]([CH3:14])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH3:13])[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]([CH3:13])[C:9]([Cl:12])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 9856017HCID 9856017, compound

Product 1

HCID 20607402HCID 20607402, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 36A (60 mg, 0.263 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (55 mg, 0.289 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 36 as a white solid. mp 87-89° C.; MS (CI/NH3) m/e 229 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.35 (s, 3H), 2.39 (s, 3H), 2.91 (s, 6H), 3.90 (mn, 1H), 4.24 (dd, J=8, 12 Hz, 1H), 4.42 (dd, J=3, 11 Hz, 1H), 7.38(d, J=8 Hz, 2H), 7.44 (d, J=3 Hz, 1H), 7.68 (d, J=8 Hz, 2H), 7.93 (d, J=3 Hz, 1H); Analysis calculated for C11H17N2ClO.1.1C7H8O3S.0.2H2O: C, 53.26; H, 6.26; N, 6.64; Found: C, 53.17; H, 6.27; N, 6.60; [α]25D=−4.6° (c=0.80, 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-e9c0ccb4f3044376aaeba88d94498104
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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