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

HRID 1785535

Reaction equation

HRID 1785535 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-5ba29fd898794ebf8e3230da2c8c99f0
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Linked notes

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