Ethylenediaminetetraacetic Acid → HCID 18980051, compound

HRID 2392549Notes

Reaction equation

HRID 2392549 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](I)=[C:9]([O:14][CH3:15])[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1.[CH2:18](C([Sn])=C(CCCC)CCCC)[CH2:19]CC.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH:18]=[CH2:19])=[C:9]([O:14][CH3:15])[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 6212ChloroformHCID 18980002HCID 18980002, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 18980051HCID 18980051, compound

Reagents, catalysts & solvents 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)CatalystHCID 1140TolueneSolvent

Procedure

8-Chloro-4-iodo-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.21 g) was suspended in toluene (5 mL) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (45 mg) was added, followed by tributylvinyltin (0.23 mL). The resulting mixture was stirred at reflux for 17 hours, cooled to room temperature, poured into saturated aqueous ethylenediaminetetraacetic acid (10 mL), and extracted with tetrahydrofuran:ether (1:1). The combined extracts were dried and evaporated to yield a yellow powder. Chromatography, with chloroform as the eluent, yielded the title compound as a white powder (80 mg); mp 212°-214° C. (dec); NMR: 11.44 (s,1), 7.55 (m,1), 7.30 (m,2), 6.69 (dd,1, J=17.7, 11.6), 5.90 (dd,1, J=17.7, 1.8), 5.52 (dd,1, J=11.5, 1.8), 3.8 (s,3). Analysis for C13H10ClNO3.0.2 H2O: Calculated: C, 58.42; H, 3.92; N, 5.24: Found: C, 58.48; H, 3.87; N, 5.06.

Workup

  1. temperatureat reflux for 17 hours
  2. extractionextracted with tetrahydrofuran:ether (1:1)
  3. customThe combined extracts were dried
  4. customevaporated
  5. customto yield a yellow powder

Sources & evidence

ORD record
ord-ab66985f40fa465eb7d7a6810ed9cc93
Source dataset
uspto-grants-1998_09
Patent number
US05801168

Reaction notes

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