Potassium Iodide → HCID 15476351, compound

HRID 380188Notes

Reaction equation

HRID 380188 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 180-1820° 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+). Anal. Calcd. for C36H30N2S: C, 82.76; H, 5.79; N, 5.36; and S, 6.12. Found: C, 82.41; H, 5.52; N, 5.25; and 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-637d64fa5aac4470bc532b1f4ae5aec5
Source dataset
uspto-grants-2001_10
Patent number
US06300502B1

Reaction notes

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