1-Naphthyl Isothiocyanate → HCID 59857370, compound

HRID 555401

Reaction equation

[C:1]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[O:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:19]1([N:29]=[C:30]=[S:31])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[C:1]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:30]([NH:29][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[S:31])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1b (40 mg, 0.17 mmol) and 1-naphtylisothiocyanate (34 mg, 0.18 mmol) in dioxane (2 mL) was heated at 60° C. for 6 h. More 1-naphtylisothiocyanate (34 mg, 0.18 mmol) was added and the mixture was heated at 60° C. for 8 days. The mixture was concentrated and the residue was purified by column chromatography on silica gel using a continuous gradient from 0% to 40% ethyl acetate in hexanes as eluent to afford 102a which was directly used in the next step. [M−H]−=426.18.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography on silica gel using a continuous gradient from 0% to 40% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record: ord-ff6f066617144174b7fa06cc4e5ab556
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053450B2

Linked notes

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