Phosphorus oxychloride → HCID 178425403, compound

HRID 431296Notes

Reaction equation

HRID 431296 reaction equation
P(Cl)(Cl)([Cl:3])=O.[ClH:6].[CH3:7][C:8]1[CH:9]=[C:10]([CH:26](O)[CH2:27][NH+:28]=[C:29]([NH2:31])[NH2:30])[CH:11]=[C:12]([CH3:25])[C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C.CCOCC>[ClH:3].[Cl:6][CH:26]([C:10]1[CH:9]=[C:8]([CH3:7])[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[C:12]([CH3:25])[CH:11]=1)[CH2:27][NH:28][C:29]([NH2:31])=[NH2+:30]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 131724229HCID 131724229, compound

Product 1

HCID 178425403HCID 178425403, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Phosphoryl Chloride (3.3 mL,3.54 mmol) was added to a solution of 14 (40.2 mg, 0.10 mmol) in DMF (1 ml). Following stirring under N2 for 24 hrs, the cmde product was isolated by diluting with Et2O. The product was then purified by recrystillization from CHCl3Et2O/EtOH. Giving pure compound 15 (31.2 mg, 74%) as an off-white solid: 1H NMR (270 MHz, MeCN d3) δ8.14(d, 1H, I=8.2 Hz, ArNO2), 8.07(d, J=8.2 Hz, 1H, ArNO2), 7.81 (t, J=8.2 Hz, 1H, ArNO2), 7.59(t, J=8.2 Hz, 1H, ArNO2), 7.49(t, J=5.2 Hz, 1H, RCH2NH), 7.19(s, 2H, Ar-H), 5.20.(s, 2H, ArOCH2 Ar(NO2)), 5.04(m, 1H, ArCH(OH)), 3.71(m, 2H, CH2—NH), 2.24(s, 6H, ArCH) 13C NMR (67.5 MHz, MeOHd4) δ157.4, 156.1, 147.4, 134.1, 133.7, 133.4, 131.5, 128.8, 128.5, 127.9, 124.5, 70.1, 60.3, 48.3, 15.2;

Workup

  1. customthe cmde product was isolated
  2. customThe product was then purified by recrystillization from CHCl3Et2O/EtOH

Sources & evidence

ORD record
ord-b50e793421794b7d95e0b7849a87a136
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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