Diethyl Ether → HCID 18763313, compound

HRID 431090Notes

Reaction equation

HRID 431090 reaction equation
[NH2:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Br:13])[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.[NH2:1][CH:2]([CH3:14])[CH2:3][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 18763314HCID 18763314, compound

Product 1

HCID 18763313HCID 18763313, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 47A (39 mg, 0.185 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (37 mg, 0.14 mmol) and stirred for 5 minutes. 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 47 as a white solid. mp 140-142° C.; MS (CI/NH3) m/e 279 (M+H)+; 311 (M+NH4)+ 1H NMR (D2O, 300 MHz) δ: 1.38 (d, J=7 Hz, 3H), 2.08-2.25 (m, 2H), 2.41 (s, 3H), 3.65 (dd, J=7, 13 Hz, 1H), 4.20-4.32 (m, 2H), 7.38 (d, J=8 Hz, 2H), 7.69 (d, J=8 Hz, 2H), 7.87 (d, J=3 Hz, 1H), 8.09 (d, J=0.0 Hz, 1H). Analysis calculated for C9H12N2BrClO.C7H8O3S: C, 42.50; H, 4.43; N, 6.20; Found: C, 42.58; H, 4.60; N, 5.94.

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-767f98bacf734e63a74cc729ef32fa99
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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