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

HRID 896988Notes

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-5e01c8de8abb4dabb5ac4985fbaa6971
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921756B2

Reaction notes

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