Sodium Hydroxide → 5-(6-Carboxyhexyl)-1-(3-oxooctyl)hydantoin

HRID 1395587Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 204369375-(6-Ethoxycarbonylhexyl)-1-(3-oxo-octyl)hydantoin

Product 1

HCID 204369575-(6-Carboxyhexyl)-1-(3-oxooctyl)hydantoin

Procedure

Diethyl 2-(3-oxooctylamino)nonanedioate (7.7 g) prepared by the method described in Example 1B was treated with potassium cyanate and hydrochloric acid to give 5-(6-ethoxycarbonylhexyl)-1-(3-oxo-octyl)hydantoin. Hydrolysis of this ester using sodium hydroxide solution gave 5-(6-carboxyhexyl)-1-(3-oxooctyl)hydantoin as a viscous oil, which crystallised to a low-melting solid.

Sources & evidence

ORD record: ord-2bc4851f075e45c581b0f35c030618a3
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04204068

Reaction notes

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