Triphenylphosphine → 1-(4-Nitrophenyl)-4-(2-phenylsulfanylethyl)-1,4-dihydrotetrazol-5-one

HRID 1071175Notes

Reaction equation

HRID 1071175 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[N:13]=[N:12][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1([S:22][CH2:23][CH2:24]O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[N:13]([CH2:24][CH2:23][S:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[N:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 696852-(Phenylthio)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178518974HCID 178518974, compound

Product 1

HCID 224717701-(4-Nitrophenyl)-4-(2-phenylsulfanylethyl)-1,4-dihydrotetrazol-5-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Nitrophenyl)-5-tetrazolone (Example 8) (153 mg, 0.74 mmol), 2-hydroxyethyl phenyl sulfide (0.1 mL, 0.74 mmol), and triphenylphosphine (194 mg, 0.74 mmol) were suspended in tetrahydrofuran (2.5 mL). Diethyl azodicarboxylate (0.12 mL, 0.74 mmol) was added dropwise. After 12 hours the mixture was concentrated in vacuo to an oil. Silica gel chromatography (9:1 hexane/ethyl acetate) afforded a solid (230 mg, 90%). 1H NMR (CDCl3, 300 MHz) δ 8.30 (d, 9.2 Hz, 2H), 8.13 (d, 9.2 Hz, 2H), 7.37 (d, 7.0 Hz, 2H), 7.20 (d, 7.0 Hz, 2H), 7.12 (m, 1H), 4.19 (t, 6.6 Hz, 2H), 3.32 (t, 6.6 Hz, 2H); MS (CI) m/z 344 (MH+).

Workup

  1. concentrationAfter 12 hours the mixture was concentrated in vacuo to an oil

Sources & evidence

ORD record
ord-adf84d60802e4270908755e3e12de3a7
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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