Triethylamine → HCID 23053765, compound

HRID 1650150Notes

Reaction equation

Br[CH:2]([CH2:12]Br)[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:4].[CH2:14]([NH:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:14]([N:21]1[CH2:22][CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:12][CH:2]1[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:4])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 48.5 g (154 mmoles) of n-hexyl 2,3-dibromopropionate (II, Z=O(CH2)5CH3) in 100 ml of dry benzene stirred at 40° C. is added dropwise to a warm solution (80° C.) of 37 g (154 mmoles) of N,N'-dibenzylethylenediamine and 55 ml of triethylamine in 100 ml benzene. The mixture was stirred for 3 hours at 80° C. After cooling and filtration of the triethylammonium chloride, the solution was evaporated off and the crude residue treated with diethyl ether and washed with water. The organic layer was dried (MgSO4), evaporated and chromatographed on a silica gel column using diethyl ether/petroleum ether (10:90, in vol.) as eluent, yielding 52.5 g (86.5%) of the title compound as an oil.

Workup

temperatureAfter cooling
filtrationfiltration of the triethylammonium chloride
customthe solution was evaporated off
additionthe crude residue treated with diethyl ether
washwashed with water
dry with materialThe organic layer was dried (MgSO4)
customevaporated
customchromatographed on a silica gel column

Sources & evidence

ORD record: ord-44fa1937d69e45b6b5617527d4cf2a3e
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923870

Reaction notes

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