Triethylamine → HCID 374541, compound

HRID 1899061Notes

Reaction equation

CN[N:3](NC)[C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](CC)=[C:7]([N+:16]([O-:18])=[O:17])[C:6]=1Cl.Cl.[Cl:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][Cl:30].[CH3:31][CH2:32][N:33]([CH2:36]C)[CH2:34]C>>[CH3:34][N:33]([CH2:32][CH2:31][NH:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[C:6]=1[N:27]([CH2:28][CH2:29][Cl:30])[CH2:26][CH2:25][Cl:24])[CH3:36]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 522769Bis(2-chloroethyl)amine hydrochloride

HCID 86749965HCID 86749965, compound

Product 1

HCID 374541HCID 374541, compound

Procedure

Reaction of this amide (XI: Z=NHCH2CH2NMe2) with bis(2-chloroethyl)amine hydrochloride and Et3N as above, followed by chromatography on silica gel and elution with EtOAc/MeOH (9:1) gave N-(N,N-dimethylaminoethyl) 2-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzamide (20 ) (Ie: R=CONHCH2CH2NMe2), mp (EtOAc/petroleum ether) 115°-118° C. 1H NMR (CDCl3) δ 8.63 (s, 2 H, ArH4), 7.41 (br, 1 H, CONH), 3.74 (t, J=6.3 Hz, 4 H, CH2Cl), 3.59 (t, J=5.8 Hz, 2 H, CONHCH2), 3.55 (t, J=6.3 Hz, 4 H, NCH2CH2Cl), 2.56 (t, J=5.8 Hz, 2 H, CH2NMe2), 2.27 (s, 6 H, NMe2). 13C NMR 164.70 (CO), 145.93 (C-2), 144.86, 141.94 (C-3,5), 135.68 (C-1), 129.63 (C-4), 123.16 (C-6), 57.51 (CONHCH2), 54.82 (NCH2CH2Cl), 45.12 (NMe2), 41.39 (NCH2CH2Cl), 37.67 (CONHCH2). Anal. (C15H21Cl2N5O5) C,H,N,Cl. (The hydrochloride salt was too hygroscopic to handle).

Workup

washfollowed by chromatography on silica gel and elution with EtOAc/MeOH (9:1)

Sources & evidence

ORD record: ord-935fdd6f133e4781b3bef89b94cdaba1
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571845

Reaction notes

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