Diethyl Ether → HCID 20607434, compound

HRID 431084Notes

Reaction equation

HRID 431084 reaction equation
[CH3:1][N:2]([CH3:14])[C@@H:3]([CH3:13])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[N:10][CH:11]=1.O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(OCC)C>C(OCC)(=O)C>[C:16]1([CH3:26])[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[CH3:1][N:2]([CH3:14])[C@@H:3]([CH3:13])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 12112021HCID 12112021, compound

Product 1

HCID 20607434HCID 20607434, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 27A (150 mg, 0.701 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (140 mg, 0.736 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 27 as a white hygroscopic solid. mp 80-82° C.; MS (CI/NH3) m/e 215 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.42 (d, J=7 Hz, 3H), 2.39 (s, 3H), 2.91 (d, J=1 Hz, 6H), 3.91 (m, 1H), 4.28 (dd, J=6, 11 Hz, 1H), 4.40 (dd, J=4, 12 Hz, 1H), 7.37 (d, J=8 Hz, 2H), 7.44-7.53 (m, 2H), 7.69 (d, J=8 Hz, 2H), 8.11 (d, J=3 Hz, 1H); Analysis calculated for C10H15N2ClO.1.03C7H8O3S.0.08H2O: C, 52.53; H, 5.99; N, 7.11; Found: C, 52.93; H, 5.88; N, 6.71; [α]25D=−3.3° (c=1.3, 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-ff94f894b16149f287a55a7c1f196572
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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