Triethylamine → Benzyl 2-(4-chloro-3-nitrobenzamido)acetate

HRID 1399431Notes

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:50]([C:51](Cl)=[O:52])=[CH:49][C:48]=1[N+:56]([O-:58])=[O:57]>>[Cl:46][C:47]1[CH:55]=[CH:54][C:50]([C:51]([NH:1][CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[O:52])=[CH:49][C:48]=1[N+:56]([O-:58])=[O:57]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 1234774-Chloro-3-nitrobenzoyl chloride

HCID 409140Benzyl glycinate

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

Product 1

HCID 7899173Benzyl 2-(4-chloro-3-nitrobenzamido)acetate

Procedure

The reaction of 4-chloro-3-nitrobenzoyl chloride (prepared from 4-chloro-3-nitrobenzoic acid, 1.0 g and SOCl2, 10 mL) with benzyl glycinate.PTS salt (2.0 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 pale green color solid (1.38 g, 80%), mp 84-86° C. 1H NMR (400 MHz, CDCl3): δ 8.31 (1H, d, J=2.0 Hz), 7.95 (1H, dd, J=8.4, 2.0 Hz), 7.65 (1H, d, J=8.4 Hz), 7.38 (5H, br s), 6.73 (1H, br s), 5.24 (2H, s), 4.29 (2H, d, J=4.8 Hz); LC-MS (negative ion mode): m/z 347 (M−H)−.

Sources & evidence

ORD record: ord-206a018baa454ecda5311f51d46bbb41
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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