2-Bromoethanol → Diethyl 2-amino-6-[(2-hydroxy-ethoxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate

HRID 1954343Notes

Reaction equation

[Na].[NH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:18][C:19](=[O:22])[NH:20][OH:21])[CH:9]=[CH:10]2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].Br[CH2:29][CH2:30][OH:31]>>[NH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:18][C:19](=[O:22])[NH:20][O:21][CH2:29][CH2:30][OH:31])[CH:9]=[CH:10]2)[C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

Reactant 2

HCID 108982-Bromoethanol

HCID 86755843Diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium

Product 1

HCID 15411825Diethyl 2-amino-6-[(2-hydroxy-ethoxycarbamoyl)-methyl]-azulene-1,3-dicarboxylateYield 15%

Procedure

In an analogous manner to that described in Example 1, from diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium and 2-bromoethanol the title compound of m.p. 190-192° C. is obtained in 15% yield.

Sources & evidence

ORD record: ord-8548b00246414192b61a5bdf16d682ce
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121322

Reaction notes

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