Triethylamine → HCID 68920532, compound

HRID 660508Notes

Reaction equation

HRID 660508 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:35][CH3:36])CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:3]=[CH:2]/[C:1](=[O:8])[C:36]2[CH:35]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68920532HCID 68920532, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

1-Phenylpropenone (58 mg, 0.44 mmol), 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (200 mg, 0.37 mmol), Pd(OAc)2 (4 mg), triethylamine (372 mg, 0.367 mmol), and acetonitrile (3 mL) are placed in a microwave vial and heated at 120° C. for 15 min. The mixture is filtered over Celite and washed with acetonitrile. The filtrate is evaporated to give the title compound which is used directly in the next step.

Workup

  1. filtrationThe mixture is filtered over Celite
  2. washwashed with acetonitrile
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-f9057d6bb4df427fb0fac0634fccc14c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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