Diethyl Ether → HCID 20607433, compound

HRID 431081Notes

Reaction equation

HRID 431081 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 12112026HCID 12112026, compound

Product 1

HCID 20607433HCID 20607433, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product 11A (36 mg, 0.158 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (33 mg, 0.173 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. It was then dried under vacuum to provide 11 as a white hygroscopic solid. mp 58-60° C.; MS (CI/NH3) m/e 229 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.37 (s, 3H), 2.40 (s, 3H), 2.88 (bs, 3H), 2.95 (bs, 3H), 3.87 (m, 1H), 4.25 (m, 1H), 4.41 (m, 1H), 7.38 (d, J=8 Hz, 2H), 7.47 (d, J=3 Hz, 1H), 7.70 (d, J=8 Hz, 2H), 7.95 (d, J=3 Hz, 1H); Analysis calculated for C11H17N2ClO.1.45C7H8O3S.0.40H2O: C, 52.31; H, 6.10; N, 5.77; Found: C, 52.00; H, 6.12; N, 6.06; [α]25 D=+3.8° (c=0.21, MeOH).

Workup

  1. stirringstirred for an additional 5 minutes
  2. customThe ether was decanted
  3. customIt was then dried under vacuum

Sources & evidence

ORD record
ord-bd60eed847e040539cdcfc3422a8aafa
Source dataset
uspto-grants-2003_12
Patent number
US06656958B2

Reaction notes

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