Diethyl Ether → HCID 20607397, compound

HRID 431088Notes

Reaction equation

HRID 431088 reaction equation
[NH2:1][C@H:2]([CH3:20])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[C:16]([CH:18]=[CH2:19])[CH:15]=[CH:14][N:13]=2)[C:8]([Cl:11])=[N:9][CH:10]=1.O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(OCC)C>C(OCC)(=O)C>[C:22]1([CH3:32])[CH:23]=[CH:24][C:25]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:26][CH:27]=1.[NH2:1][C@H:2]([CH3:20])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[C:16]([CH:18]=[CH2:19])[CH:15]=[CH:14][N:13]=2)[C:8]([Cl:11])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 20607396HCID 20607396, compound

Product 1

HCID 20607397HCID 20607397, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 38B (58 mg, 0.201 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (42 mg, 0.221 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 38 as a light yellow solid. mp 47-49° C.; MS (CI/NH3) m/e 290 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.48 (d, J=7 Hz, 3H), 2.35 (s, 3H), 3.87 (m, 1H), 4.14 (m, 1H), 4.31 (dd, J=4, 10 Hz, 1H), 7.10 (d, J=6 Hz, 2H), 7.29 (d, J=8 Hz, 2H), 7.45 (d, J=16 Hz, 2H), 7.64 (d, J=8 Hz, 2H), 7.68 (d, J=3 Hz, 1H), 7.93 (d, J=3 Hz, 1H), 8.45 (d, J=6 Hz, 2H); Analysis calculated for C15H16N3ClO.1.19C7H8O3S.0.95H2O: C, 54.75; H, 5.40; N, 8.21; Found: C, 54.43; H, 5.36; N, 8.61; [α]25D=−1.6° (c=0.55, 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-c923bdf86b5b45e1bdade8e520dfdafc
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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