O,O-Dipyridin-2-yl carbonothioate → 2-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

HRID 600772

Reaction equation

HRID 600772 reaction equation
[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH2:14])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)[CH3:2].[C:15](=[S:30])(OC1C=CC=CN=1)OC1C=CC=CN=1>ClCCl>[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:7]([CH2:6][CH:5]=1)=[CH:8][CH:9]=[CH:10][C:11]=2[N:14]=[C:15]=[S:30])[CH3:2]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 230669967-Ethoxy-5,8-dihydronaphthalen-1-amine

Product 1

HCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of Example 1E (200 mg, 1.06 mmol) in dichloromethane (2.5 mL) was added to a solution of O,O-dipyridin-2-yl thiocarbonate (246 mg, 1.06 mmol) in dichloromethane (5 mL) at room temperature. After stirring at room temperature for 18 hours, the mixture was concentrated, then filtered through silica gel and eluted with 5% ethyl acetate-hexane. Evaporation of the filtrate in vacuo afforded the title compound as a pale pink solid, 225 mg (92%). 1H NMR (DMSO-d6) δ 7.21-7.27 (m, 3H), 4.86 (t, 1H, J=3.6 Hz), 3.81 (q, 2H, J=7.0 Hz), 3.49 (q, 2H, 4.4 Hz), 3.35 (t, 2H, J=5.2 Hz), 1.27 (t, 3H, J=7.0 Hz); MS (DCI+) m/z 232 (M+H).

Workup

  1. concentrationthe mixture was concentrated
  2. filtrationfiltered through silica gel
  3. washeluted with 5% ethyl acetate-hexane
  4. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-3c6d5ac5b5b249a09758f315337759dd
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Linked notes

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