Acetic Acid → HCID 178517211, compound

HRID 642085Notes

Reaction equation

HRID 642085 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O1C[CH2:17][CH2:16][N:15]([CH2:19][C:20]2[CH:36]=[CH:35][C:23]([O:24][C:25]3[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=3)=[CH:22][CH:21]=2)[CH2:14]1.[C:37](O)(=[O:39])C>>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:32][NH:31][C:29](=[O:30])[C:28]1[CH:27]=[CH:26][C:25]([O:24][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][N:15]3[CH2:16][CH2:17][O:39][CH2:37][CH2:14]3)=[CH:36][CH:35]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 886955-IodoisatinHCID 68408653HCID 68408653, compound

Product 1

HCID 178517211HCID 178517211, compoundYield 67%

Conditions

Temperature
100 °C

Procedure

Into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 4-[4-(1,3-oxazinan-3-ylmethyl)phenoxy]benzohydrazide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 194 mg of the title compound (67%) as a yellow solid in 98.9% purity by HPLC (Rt: 3.27, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-e0b93769a0ae4c4999f3975af628d131
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…