Triethylamine → Benzyl 2-(2-chloro-5-nitrobenzamido)acetate

HRID 1399432Notes

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.[Cl:46][C:47]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][C:48]=1[C:49](Cl)=[O:50]>>[Cl:46][C:47]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][C:48]=1[C:49]([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:50]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 117637Benzoyl chloride, 2-chloro-5-nitro-

HCID 409140Benzyl glycinate

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

Product 1

HCID 18274893Benzyl 2-(2-chloro-5-nitrobenzamido)acetateYield 82%

Procedure

The reaction of 2-chloro-5-nitrobenzoyl chloride (prepared from 2-chloro-5-nitrobenzoic acid, 1.0 g and SOCl2, 10 mL) with benzyl glycinate.PTS salt (1.9 g, 5.9 mmol) in the presence of triethylamine (2.0 mL, 14.88 mmol) as described in intermediate 1 gave the title compound as a colorless solid (1.42 g, 82%), mp 116-118° C. 1H NMR (400 MHz, CDCl3): δ 8.54 (1H, d, J=2.8 Hz), 8.23 (1H, dd, J=8.6, 2.6 Hz), 7.61 (1H, d, J=8.8 Hz), 7.38 (5H, br s), 6.88 (1H, br s), 5.24 (2H, s), 4.32 (2H, d, J=4.8 Hz); LC-MS (positive ion mode): m/z 349, 351 (M+H)+.

Sources & evidence

ORD record: ord-d1626e5d189448748733b9290641dd37
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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