Ethylenediamine → (9-Chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

HRID 48326

Reaction equation

[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][N:13](C)[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].FC1C([Cl:32])=CC=CC=1C(O)=O.CNCCN.C(N)CN>>[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][NH:13][C:12]2[C:18]([Cl:32])=[CH:19][CH:20]=[CH:21][C:11]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 8014N-Methylethylenediamine

HCID 3029313-Chloro-2-fluorobenzoic acid

HCID 72957243(1-Methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

Product 1

HCID 86585810(9-Chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

Procedure

(9-chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester was prepared in an analogous fashion to (1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester, prepared in Example 1, by replacing 2-fluorobenzoic acid with 2-fluoro-3-chlorobenzoic acid and N-methylethylenediamine with ethylenediamine.

Workup

customprepared in Example 1

Sources & evidence

ORD record: ord-156eba81e47e464d806a53a6449d9179
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703387B2

Linked notes

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