Triethylamine → 3-Ethyl-5-{2-ethyl-3-[(3-ethylbenzothiazolin-2-ylidene) ethylidene]isoindol-1(3H)-ylidene}-rhodanine

HRID 437324Notes

Reaction equation

HRID 437324 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([N:8]1[C:16](OC)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[C:9]1[CH:19]=[CH:20][C:21]1[S:22][C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[N+:25]=1[CH2:26][CH3:27])[CH3:7].[CH2:32]([N:34]1[C:38](=[O:39])[CH2:37][S:36][C:35]1=[S:40])[CH3:33].C(N(CC)CC)C>CO>[CH2:32]([N:34]1[C:38](=[O:39])[C:37](=[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[CH:19][CH:20]=[C:21]3[N:25]([CH2:26][CH3:27])[C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[S:22]3)[N:8]2[CH2:6][CH3:7])[S:36][C:35]1=[S:40])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 820983-EthylrhodanineHCID 867348792-[2-(2-Ethyl-3-methoxyisoindol-1-yl)vinyl]-3-ethylbenzothiazolium perchlorate

Product 1

HCID 536936043-Ethyl-5-{2-ethyl-3-[(3-ethylbenzothiazolin-2-ylidene) ethylidene]isoindol-1(3H)-ylidene}-rhodanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(2-Ethyl-3-methoxyisoindol-1-yl)vinyl]-3-ethylbenzothiazolium perchlorate (0.5 g) and 3-ethylrhodanine (0.3 g) were dissolved in a 1:1 acetronitrile/methanol solution. Triethylamine was added and the reaction mixture heated to reflux for 10 minutes. The dyes which separated out was dissolved in chloroform and passed through a column of silica gel. After recrystallization from a mixture of chloroform and methanol the dye melted at 252°-253° C. pyridine/methanol λ max 661 nm.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 10 minutes
  3. customThe dyes which separated out
  4. dissolutionwas dissolved in chloroform
  5. customAfter recrystallization
  6. additionfrom a mixture of chloroform and methanol the dye melted at 252°-253° C. pyridine/methanol λ max 661 nm

Sources & evidence

ORD record
ord-2c75d6926a96415f90a14cef7c2196e4
Source dataset
uspto-grants-1977_06
Patent number
US04030932

Reaction notes

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