Ethanolamine → HCID 9899143, compound

HRID 1861868Notes

Reaction equation

HRID 1861868 reaction equation
N(CC1CCCC1)=[N+]=[N-].[CH:10]1([CH2:15][N:16]=[C:17]=[S:18])[CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:19]([CH2:21][NH2:22])[OH:20]>>[CH:10]1([CH2:15][NH:16][C:17]([NH:22][CH2:21][CH2:19][OH:20])=[S:18])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 11137259HCID 11137259, compoundHCID 18621695HCID 18621695, compound

Product 1

HCID 9899143HCID 9899143, compoundYield 63%

Procedure

The intermediate azidomethylcyclopentane was obtained from commercially available cyclopentanemethanol as described in General Procedure D. Spectroscopic data: 1H NMR (CDCl3, 300 MHz) δ 3.18 (d, J=10.0 Hz, 2H), 2.23-2.05 (m, 1H), 1.87-1.74 (m, 2H), 1.68-1.55 (m, 4H), 1.30-1.15 (m, 2H). The azide was then converted into cyclopentylmethyl isothiocyanate, which was reacted with ethanolamine to afford the title compound (12.68 g, 63%) according to General Procedure A. Spectroscopic data: 1H NMR (D6, DMSO, 300 MHz) δ 7.46 (br s, 1H), 7.31 (br s 1H), 4.72 (br s, 1H), 3.5-3.38 (m, 4H), 3.25 (br s, 2H), 2.03 (quintet, J=6.4 Hz, 1H), 1.70-1.57 (m, 3H), 1.55-1.41 (m, 3H), 1.20-1.10 (m, 2H).

Sources & evidence

ORD record
ord-7ab0814af2314944b51fea4c422d470f
Source dataset
uspto-grants-2003_03
Patent number
US06534542B2

Reaction notes

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