Triphenylphosphine → HCID 67139716, compound

HRID 1591964Notes

Reaction equation

HRID 1591964 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][NH:10][S:9]2(=[O:15])=[O:14])=[CH:5][CH:4]=1.O[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][N:10]([CH2:25][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[S:9]2(=[O:15])=[O:14])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 588428642-(4-Methoxybenzyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 178418642HCID 178418642, compound

Product 1

HCID 67139716HCID 67139716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title B compound, 2-(4-methoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (128 mg, 0.5 mmol), 4-hydroxypyridine (109 mg, 1 mmol) and triphenylphosphine (262 mg, 1 mmol) are put into a small reaction vessel under argon and dissolved in 10 mL of THF. This solution is stirred in an ice/water bath and diethyl azodicarboxylate (174 mg, 1 mmol) diluted with an equal volume of THF is added dropwise to the stirred cold solution. The reaction is allowed to stir 16 h while the ice bath slowly warms to RT. The solvent is evaporated on the rotary evaporator, then the residue is taken up in a minimal amount of CH2Cl2 and chromatographed on a 10 g RediSep silica gel column, using a gradient from 1 to 5% EtOAc in CH2Cl2 over 15 to 20 min to afford 2-(4-methoxybenzyl)-1,1-dioxo-5-pyridin-4-ylmethyl-1,2,5-thiadiazolidin-3-one: [M+1]+=348.

Workup

  1. additionis added dropwise to the stirred cold solution
  2. customslowly warms to RT
  3. customThe solvent is evaporated on the rotary evaporator
  4. customchromatographed on a 10 g RediSep silica gel column
  5. customover 15 to 20 min

Sources & evidence

ORD record
ord-d92148b81b634fefb66e08fd0304b2ab
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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