2-Chloro-3,5-dinitrobenzoic acid → HCID 12897330, compound

HRID 1290333Notes

Reaction equation

[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:3]=1[C:4](O)=[O:5].O=S(Cl)[Cl:19]>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:3]=1[C:4]([Cl:19])=[O:5]

Participants

Reactant 2

HCID 172472-Chloro-3,5-dinitrobenzoic acid

HCID 24386Thionyl Chloride

Product 1

HCID 12897330HCID 12897330, compound

Procedure

Reaction of commercially-available 2-chloro-3,5-dinitrobenzoic acid (X) with SOCl2 gave 2-chloro-3,5-dinitrobenzoyl chloride (XI: Z=Cl), which was quenched with ammonia to give 2-chloro-3,5-dinitrobenzamide (XI: Z=NH2). A solution of this amide (1.00 g, 4.07 mmol) and Et3N (1.42 g, 10 mmol) in ρ-dioxane (30 mL) was 0356 treated with N,N-bis(2-chloroethyl)amine hydrochloride (1.45 g, 8.14 mmol) at 50° C. for 18 h. The mixture was then poured into water and extracted with EtOAc to give an oil, which was chromatographed on silica gel. Elution with EtOAc/petroleum ether (1:1) gave 2-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzramide (19) (Ie: R=CONH2) (1.15 g, 80%), mp (CHCl3 /petroleum ether) 123°-124° C. 1H NMR (CD3SOCD3) δ8.70 (d, J=2.7 Hz, 1 H, H-4), 8.49 (d, J=2.7 Hz, 1 H, H-6), 7.68, 7.35 (2xbr, 2H, CONH2), 3.80, 3.61 (2.xt, J=6.9 Hz, y 8H. NCH2CU2Cl). 13C NMR δ167.94 (CONH2), 147.27 (C-2), 147.2 0. 142.84 (C-3,5), 137.70 (C-1), 128.40, 123.24 (C-4:6), 55.84 (CH2N), 42.28 ) (CH2CI). Anal. (C11H12Cl2,N4O5) C,H,N,Cl.

Sources & evidence

ORD record: ord-f090ad5b80f3422a9088b7ed4676fb19
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750782

Reaction notes

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