4-Nitrophenol → [2-Phenyl-1-thiophene-2-sulfonylaminoethyl]-phosphonic acid mono-(4-nitrophenyl) ester ammonium salt

HRID 993097Notes

Reaction equation

[C:1]1([CH2:7][CH:8]([P:18](=[O:21])([OH:20])[OH:19])[NH:9][S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].ClC(Cl)(Cl)C#N>N1C=CC=CC=1>[NH4+:9].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:21][P:18]([CH:8]([NH:9][S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:12])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:19])[O-:20])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 105 °C

Procedure

To sealed tube containing phosphonic acid (xiii) (50 mg; 0.14 mmol) and sublimed 4-nitrophenol (24 mg; 0.17 mmol) was added pyridine (0.7 mL) and trichloroacetonitrile (100 μL; 1.0 mmol). The reaction was heated to 105° C. for 6 hrs then was cooled and concentrated. The residue was purified by flash chromatography (chloroform-methanol-concentrated ammonium hydroxide; 8:2:0.25) to yield the ammonium salt 44 (36.4 mg, 52%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 2.83 (td, J=9, 14 Hz, 1H, CHPh), 3.23-3.29 (m, 1H, CHPh), 3.95-4.02 (m, 1H, NCHP), 6.85 (dd, J=4, 5 Hz, 1H, Ar—H), 7.08-7.20 (m, 6H, Ar—H), 7.27-7.31 (m, 2H, Ar—H), 7.52 (dd, J=1.5, 5 Hz, 1H, Ar—H), 8.12-8.16 (m, 2H, Ar—H); 31P NMR: (162 MHz, CD3OD) δP 16.7; 13C NMR: (100 MHz, CD3OD) δP 38.1, 122.0, 125.9, 127.3, 128.3, 129.2, 130.6, 132.2, 132.3, 144.4, 144.5.

Workup

customTo sealed tube
temperaturethen was cooled
concentrationconcentrated
customThe residue was purified by flash chromatography (chloroform-methanol-concentrated ammonium hydroxide; 8:2:0.25)

Sources & evidence

ORD record: ord-e0ddbba06dca488887718fab97c99e50
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472406B1

Reaction notes

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