Triethylamine → HCID 86691356, compound

HRID 2167218Notes

Reaction equation

HRID 2167218 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)=[O:2].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].CCN(CC)CC>C1COCC1>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])=[O:8])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80480N-(2-Aminoethyl)ethyleneureaHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 86691356HCID 86691356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the 4-formylbenzoyl chloride (16.5 g, 0.098 mol) in dry THF (100 ml) was added, over a period of minutes, to a suspension of 1-(2-amino-ethyl)imidazolidin-2-one (12.6 g, 0.098 mol) and Et3N (19.8 g, 0.195 mol) in dry THF (300 ml) at −35° C. During the addition, the temperature of the reaction medium was maintained between −35 and −38° C. The temperature of the reaction medium was then slowly brought back to ambient temperature over a period of 4 hours. The precipitate obtained (mainly the expected product as a mixture with triethylamine hydrochloride Et3N.HCl) was filtered off and washed with THF (twice with 20 ml). The reaction crude was solubilized in an aqueous solution of Na2CO3 (3.4 g, 0.032 mol in 40 ml of water). The expected compound was extracted several times with EtOAc (total volume: 3.5 l).

Workup

  1. additionDuring the addition
  2. temperaturethe temperature of the reaction medium was maintained between −35 and −38° C

Sources & evidence

ORD record
ord-17ca46fd092443e1bbe4bacf80810edb
Source dataset
uspto-grants-2015_06
Patent number
US09045432B2

Reaction notes

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