Glycine → 2-(3-Iodo-4-nitrobenzamido)acetic acid

HRID 1399434Notes

Reaction equation

HRID 1399434 reaction equation
NCC(O)=O.C([O-])([O-])=O.[Na+].[Na+].[I:12]([C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:18]([NH:20][CH2:21][C:22]([O:24]CC(Cl)(Cl)Cl)=[O:23])=[O:19])(=O)=O>IC1C=C(C=CC=1[N+]([O-])=O)C(Cl)=O>[I:12][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

5

Reactant 3

HCID 750GlycineHCID 10340Sodium CarbonateHCID 867131132,2,2-Trichloroethyl 2-(3-iodyl-4-nitrobenzamido)acetate

Product 1

HCID 867131122-(3-Iodo-4-nitrobenzamido)acetic acid

Reagents, catalysts & solvents 1

HCID 867131113-Iodo-4-nitrobenzoyl chlorideSolvent

Procedure

The reaction of 3-iodo-4-nitrobenzoyl chloride (prepared from 3-iodo-4-nitrobenzoic acid, 1.2 g and SOCl2, 10 mL) with glycine (0.38 g, 5.12 mmol) in the presence of Na2CO3 (0.54 g, 5.12 mmol) as described in intermediate 2 gave the title compound as a pale yellow color solid (1.3 g, 91%), mp 140-142° C. 1H NMR (400 MHz, DMSO-d6): δ 12.69 (1H, br s), 9.19 (1H, t, J=5.6 Hz), 8.52 (1H, br s), 8.05 (2H, br s), 3.96 (2H, d, J=6.0 Hz); LC-MS (negative ion mode): m/z 349 (M−H)−.

Sources & evidence

ORD record
ord-976313f8701b464cbec4d62a59243e4e
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

Loading…