alpha-Naphthyl isocyanate → HCID 68327780, compound

HRID 2274890Notes

Reaction equation

HRID 2274890 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[C:2]=[O:3].[N:14]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[NH:17][CH2:16][CH2:15]2>>[C:4]1([NH:1][C:2]([N:17]2[CH:18]3[CH2:21][CH2:22][N:14]([CH2:20][CH2:19]3)[CH2:15][CH2:16]2)=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 3984071,4-Diazabicyclo(3.2.2)nonane

Product 1

HCID 68327780HCID 68327780, compoundYield 48%

Procedure

Using general procedure A, 1-isocyanatonaphthalene (208 mg, 1.23 mmol) and 1,4-diazabicyclo[3.2.2]nonane gave the title compound as a white solid (150 mg, 48%). 1H NMR (400 MHz, CDCl3) δ 7.80-7.72 (m, 2H), 7.64 (d, J=8.0 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.44-7.35 (m, 3H), 6.65 (br s, 1H), 4.18 (br s, 1H), 3.64 (t, J=8.0 Hz, 2H), 3.09-2.91 (m, 6H), 2.08-1.93 (m, 2H) 1.74-1.66 (m, 2H) ppm. 13C NMR (100 MHz, CDCl3) δ 155.3, 134.4, 134.3, 128.9, 128.2, 126.2, 126.1, 126.0, 125.1, 121.2, 121.0, 57.6, 48.7, 46.4, 46.4, 42.2, 27.6, 27.6 ppm. Purity: >99% UPLCMS (210 nm); retention time 0.53 min; (M+1) 296.

Sources & evidence

ORD record
ord-2323d8be76fa4b66bd056589040c49e8
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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