Potassium Iodide → HCID 15476351, compound

HRID 1871163Notes

Reaction equation

HRID 1871163 reaction equation
[C:1]1([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:13]2[CH2:12][C:11]3[C:6](=CC=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:29]1([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[I-].[K+].C1O[CH2:60][CH2:59]OCCOCCOCCOCCOC1.Cl[C:63]1[CH:68]=CC=[CH:65][C:64]=1Cl>[Cu].[Cu]I>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:1]1[CH:13]=[C:12]2[C:4]([C:39]3[CH:40]=[CH:41][C:36]([N:35]([C:60]4[CH:59]=[CH:65][CH:64]=[CH:63][CH:68]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:37][C:38]=3[C:11]2([CH2:6][CH3:5])[CH2:10][CH3:9])=[CH:3][CH:2]=1

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 72391,2-DichlorobenzeneHCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 2855718-Crown-6HCID 67291382HCID 67291382, compound

Product 1

HCID 15476351HCID 15476351, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
179 °C

Procedure

A mixture of 2-(9,9-diethyl-7-bromo-2-) fluorenyl benzothiazole (6.6 g., 0.015 mol.), potassium carbonate (10.3 g.,0.0746 mol.), diphenylamine (4.5 g. 0.0376 mol.), potassium iodide (9.6 g. 0.0173 mol.), copper bronze (2.0 g., 0.0317 mol.), copper (I) iodide (1.5 g., 0.0079 mol.), 18-crown-6 (0.96 g., 0.0036 mol.),and 1,2-dichlorobenzene (45 ml.) was kept at 180-182° C. for 20 hours, cooled and filtered. The filtrate was concentrated and the residue was transferred to a column of silica gel. Elution with heptane gave the product, 3.6 g.(45.5% yield), m.p. 175-178.4° C. Recrystallization from 9:1 heptane-toluene raised the m.p. to 178-180° C. Mass Spec: m/z 522, (M+). Analysis calculated for C36H30N2S: C, 82.76; H, 5.79; N, 5.36; S, 6.12. Found: C, 82.41; H, 5.52; N, 5.25; S, 5.99.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. washElution with heptane
  5. customgave the product, 3.6 g
  6. customRecrystallization from 9:1 heptane-toluene

Sources & evidence

ORD record
ord-e1585c0e76a540c7b3931fc3f3ea0b44
Source dataset
uspto-grants-2000_08
Patent number
US06100405

Reaction notes

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