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

HRID 1004647Notes

Reaction equation

HRID 1004647 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, 2 H), 8.13 (d, 9.2 Hz, 2 H), 7.37 (d, 7.0 Hz, 2 H), 7.20 (d, 7.0 Hz, 2 H), 7.12 (m, 1 H), 4.19 (t, 6.6 Hz, 2 H), 3.32 (t, 6.6 Hz, 2 H); 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-c1ade47f11d0448abadf486939672ff8
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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