Triphenylphosphine → HCID 67138626, compound

HRID 1591986Notes

Reaction equation

HRID 1591986 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.[I:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[I:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:10]1[S:9](=[O:15])(=[O:14])[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[C:12](=[O:13])[CH2:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 423003-Iodobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 588428642-(4-Methoxybenzyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 67138626HCID 67138626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the title B compound, 2-(4-methoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.02 g, 3.98 mmol), 3-iodo-benzyl alcohol (1.01 mL, 7.95 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in THF (50 mL) is cooled to 5° C. and treated with a solution of diethyl azodicarboxylate (1.26 mL, 8.0 mmol) in THF (10 mL). The reaction is allowed to warm to RT over 16 h. The reaction mixture is concentrated to yield a yellow oil. This is chromatographed on a 110 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:CH2Cl2) to 5:95 over 25 min. Fractions containing product are combined and concentrated to yield an oil, which spontaneously crystalizes. Trituration with Et2O yields 5-(3-iodo-benzyl)-2-(4-methoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid: mp=98-100° C.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto yield a yellow oil
  3. customThis is chromatographed on a 110 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:CH2Cl2) to 5:95 over 25 min
  4. additionFractions containing product
  5. concentrationconcentrated
  6. customto yield an oil, which
  7. customspontaneously crystalizes

Sources & evidence

ORD record
ord-eee72317b88f4812b6502a0915940a63
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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