Diethyl Ether → HCID 20607436, compound

HRID 431083Notes

Reaction equation

HRID 431083 reaction equation
[CH3:1][N:2]([CH3:21])[C@@H:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][O:5][C:6]1[CH:7]=[C:8]([Br:13])[C:9]([Cl:12])=[N:10][CH:11]=1.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(OCC)C>C(OCC)(=O)C>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[CH3:21][N:2]([CH3:1])[C@@H:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[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 12112029HCID 12112029, compound

Product 1

HCID 20607436HCID 20607436, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 22A (170 mg, 0.459 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (96 mg, 0.505 mmol) and stirred for 5 minutes. Then 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 22 as a white hygroscopic solid. mp 45-47° C.; MS (ESI+) m/e 369 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 2.39 (s, 3H), 3.06 (s, 6H), 3.13 (m, 1H), 3.37 (dd, J=5, 14 Hz, 1H), 4.02 (m, 1H), 4.18 (dd, J=6, 12 Hz, 1H), 4.30 (dd, J=3, 12 Hz, 1H), 7.30-7.43 (m, 7H), 7.68(d, J=8 Hz, 2H), 7.71 (d, J=3 Hz, 1H), 8.01 (d, J=3 Hz, 1H); Analysis calculated for C16H18N2BrClO.1.15C7H8O3S.0.60H2O: C, 49.93; H, 4.95; N, 4.84; Found: C, 49.82; H, 4.88; N, 4.72; [α]25D=+58° (c=3.0, 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-479cf2a56cc045b599d716032c63534e
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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