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Hydrochloric Acid → 5-(6-Ethoxycarbonylhexyl) hydantoin

HRID 444049
Notes
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Reaction equation

HRID 444049 reaction equation
[NH:1]([CH:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6](OCC)=[O:7])[C:2]([NH2:4])=[O:3].C1(C2CCCCCCCC=2)CCCCCCNN=1.C(Cl)(Cl)Cl.Cl>CCOCC>[CH2:20]([O:19][C:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:5]1[NH:1][C:2](=[O:3])[NH:4][C:6]1=[O:7])=[O:18])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 20436881Diethyl 2-ureidononanedioateHCID 66586414Diazabicylononene

Product 1

HCID 204370125-(6-Ethoxycarbonylhexyl) hydantoin

Reagents, catalysts & solvents 1

HCID 3283Diethyl Ether
Solvent

Procedure

A mixture of diethyl 2-ureidononanedioate (8 g) with diazabicyclononene (DBN) (1.28 g) was heated in a bath at 100° for 1 hour and the reaction mixture was shaken with chloroform and a slight excess of dilute hydrochloric acid. The chloroform phase was separated, washed with water and dried (MgSO4), and the chloroform was evaporated, to give a crystalline residue. The crystals were suspended in ether and collected, to give 5-(6-ethoxycarbonylhexyl) hydantoin, m.p. 110°-110.5° C.

Workup

  1. temperaturewas heated in a bath at 100° for 1 hour
  2. customThe chloroform phase was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe chloroform was evaporated
  6. customto give a crystalline residue
  7. customcollected

Sources & evidence

ORD record
ord-fbf728b875274360bf745e000f403f95
Source dataset
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04262128

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes