Pyridine → HCID 73793969, compound

HRID 1415096Notes

Reaction equation

HRID 1415096 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[C:6]1([C:12]2[C:17]3[S:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N+:16]=3[CH2:15][CH2:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I-].C1(S[C:33]2[S:34][C:35]3[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=3[N+:37]=2[CH2:38][CH3:39])C=CC=CC=1.N1C=CC=CC=1>C(OCC)C>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:38]([N:37]1[C:36]2[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=2[S:34][C:33]1=[C:14]1[CH2:15][N+:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18][C:17]=2[C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:13]1)[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21483495HCID 21483495, compoundHCID 706351533-Ethyl-2-(phenylsulfanyl)-1,3-benzothiazol-3-ium iodide

Product 1

HCID 73793969HCID 73793969, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,2-Dihydro-4-phenylpyrido[2,1-b]benzothiazolium perchlorate (2.0 g., 0.0055 mole), 2-phenylthio-3-ethylbenzothiazolium iodide (2.19 g., 0.0055 mole) and pyridine (30 ml.) are heated to reflux for 3 minutes, the solution is cooled, diethyl ether (30 ml.) is added and the green solution is decanted off from the oily dye. Water is added and the dye solidifies upon cooling. The solid dye is boiled out with isopropyl alcohol. The yield of dye is 1.0 g. (35% yield). The product has a melting point of 120°-128° C with an absorption maximum at 629 nm.

Workup

  1. temperatureto reflux for 3 minutes
  2. temperaturethe solution is cooled
  3. customthe green solution is decanted off from the oily dye
  4. additionWater is added
  5. temperatureupon cooling

Sources & evidence

ORD record
ord-269828678cae4135b541be0aabe5807a
Source dataset
uspto-grants-1977_01
Patent number
US04003750

Reaction notes

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