Triethylamine → 2-{2-[2-Ethyl-3-(3-ethylbenzothiazolin-2-ylidenemethyl) isoindol-1-yl]-vinyl}-3-ethylbenzoxazolium perchlorate

HRID 437323

Reaction equation

HRID 437323 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[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[O:22][C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[N+:25]=1[CH2:26][CH3:27])[CH3:7].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:43]([N+:45]1[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2[S:47][C:46]=1[CH3:54])[CH3:44].C(N(CC)CC)C>C(#N)C>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:6]([N:8]1[C:16]([CH:54]=[C:46]2[N:45]([CH2:43][CH3:44])[C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=3[S:47]2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[C:9]1[CH:19]=[CH:20][C:21]1[O:22][C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[N+:25]=1[CH2:26][CH3:27])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84711Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)HCID 867348772-[2-(2-Ethyl-3-methoxyisoindol-1-yl)vinyl]-3-ethyl-benzoxazolium perchlorate

Product 1

HCID 867348752-{2-[2-Ethyl-3-(3-ethylbenzothiazolin-2-ylidenemethyl) isoindol-1-yl]-vinyl}-3-ethylbenzoxazolium perchlorate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[2-(2-Ethyl-3-methoxyisoindol-1-yl)vinyl]-3-ethyl-benzoxazolium perchlorate (1.0 g) and 3-ethyl-2-methylbenzothiazolium p-toluenesulfonate (0.9 g) were dissolved in acetonitrile. Triethylamine was added and the reaction mixture stirred until the absorption at 520 nm disappeared. The reaction mixture was evaporated to dryness and chromatographed on silica gel. After recrystallization of the product from methanol, the melting point was 180° C. CH3CN λ max 625 nm.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customchromatographed on silica gel
  3. customAfter recrystallization of the product from methanol

Sources & evidence

ORD record
ord-abd11817a4754010927b1f70aef32e3c
Source dataset
uspto-grants-1977_06
Patent number
US04030932

Linked notes

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