4-Methoxybenzyl alcohol → HCID 67139575, compound

HRID 1592056Notes

Reaction equation

HRID 1592056 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]O)=[CH:39][CH:38]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:13])(=[O:14])[N:11]([CH2:41][C:40]3[CH:43]=[CH:44][C:37]([O:36][CH3:35])=[CH:38][CH:39]=3)[C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 67138424HCID 67138424, compound

Product 1

HCID 67139575HCID 67139575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title B compound, 5-(3-iodo-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (932 mg, 2.76 mmol) is dissolved in tetrahydrofuran (20 mL) in a 40 mL capacity septum capped vial, stirred under argon balloon. Triphenylphosphine (1.47 g, 5.51 mmol) is added as a solid and stirred until dissolved, then 4-methyoxybenzyl alcohol (0.688 mL, 5.51 mmol) is added by syringe. The stirred reaction is cooled in an ice bath, and diethyl azodicarboxylate (0.867 mL, 5.51 mmol) is added slow dropwise by syringe. The reaction is stirred 16 h and then recooled and added more diethyl azodicarboxylate (0.433 mL, 2.26 mmol). After 5H, the reaction is concentrated in vacuo, then taken up in CH2Cl2 and chromatographed on a 35 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:CH2Cl2) for 5 min, then to 5:95 over 35 min. Fractions containing product are combined, concentrated and recrystalized with EtOAc/hexanes to yield 5-(3-iodo-phenyl)-2-(4-methoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid: 1H-NMR (300 MHz, DMSO-d6) δ 3.76 (s, 3H), 4.79 (s, 2H), 4.88 (s, 2H), 6.92 (d, J=7.5, 2H), 7.27 (t, J=7.5, 1H), 7.33 (d, J=7.5, 2H), 7.39 (d, J=7.5, 1H), 7.63 (d, J=7.5, 1H), 7.67 (s, 1H).

Workup

  1. customcapped vial
  2. stirringstirred
  3. dissolutionuntil dissolved
  4. customThe stirred reaction
  5. temperatureis cooled in an ice bath
  6. stirringThe reaction is stirred 16 h
  7. concentrationAfter 5H, the reaction is concentrated in vacuo
  8. customchromatographed on a 35 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:CH2Cl2) for 5 min
  9. additionFractions containing product
  10. concentrationconcentrated
  11. customrecrystalized with EtOAc/hexanes

Sources & evidence

ORD record
ord-f481e6c6b838466fa306e37efada3133
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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