Triethylamine → Benzyl 2-(3,4-dinitrobenzamido)acetate

HRID 1399429Notes

Reaction equation

[NH2:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[N+](C1C=C([N+]([O-])=O)C=CC=1C(NCC(OCC1C=CC=CC=1)=O)=O)([O-])=O.[N+:46]([C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][C:57]=1[N+:58]([O-:60])=[O:59])[C:52](Cl)=[O:53])([O-:48])=[O:47]>>[N+:46]([C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][C:57]=1[N+:58]([O-:60])=[O:59])[C:52]([NH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:53])([O-:48])=[O:47]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 409140Benzyl glycinate

HCID 118064913,4-dinitrobenzoyl Chloride

HCID 86713106Benzyl 2-(2,4-dinitrobenzamido)acetate

Product 1

HCID 86713107Benzyl 2-(3,4-dinitrobenzamido)acetate

Procedure

The reaction of 3,4-dinitrobenzoyl chloride (prepared from 3,4-dinitrobenzoic acid, 500 mg and SOCl2, 10 mL) with benzyl glycinate.PTS salt (794 mg, 2.358 mmol) in the presence of triethylamine (1.0 mL, 7.07 mmol) as described in intermediate 1 gave the title compound as an yellow color solid (780 mg, 92%), mp 150-152° C. 1H NMR (400 MHz, CDCl3): δ 8.37 (1H, br s), 8.17 (1H, d, J=8.0 Hz), 8.00 (1H, d, J=7.6 Hz), 7.39 (5H, s), 6.79 (1H, br s), 5.26 (2H, s), 4.31 (2H, d, J=4.0 Hz); LC-MS (negative ion mode): m/z 358 (M−H)−.

Sources & evidence

ORD record: ord-540fe0b78b78443cac3cde63659f62e0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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