Triethylamine → 2-[2-(3-Chloro-2-ethylisoindol-1-yl)vinyl]-3-ethylbenzothiazolium perchlorate

HRID 437321Notes

Reaction equation

HRID 437321 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[Cl:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[CH:16]N(C)C)[N+:8]=1[CH2:20][CH3:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:33]([N+:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[S:37][C:36]=1[CH3:44])[CH3:34].C(N(CC)CC)C>C(#N)C>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[Cl:6][C:7]1[N:8]([CH2:20][CH3:21])[C:9]([CH:16]=[CH:44][C:36]2[S:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N+:35]=2[CH2:33][CH3:34])=[C:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84711Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)HCID 178462637HCID 178462637, compound

Product 1

HCID 867348732-[2-(3-Chloro-2-ethylisoindol-1-yl)vinyl]-3-ethylbenzothiazolium perchlorate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-chloro-1-dimethylaminomethylene-2-ethyl-1H-isoindolium perchlorate (0.5 g) and 3-ethyl-2-methylbenzothiazolium p-toluene sulfonate (0.5 g) were dissolved in acetonitrile and triethylamine added. After 30 minutes at room temperature the product was precipitated by the addition of ether and purified by chromatography on silica gel. After recrystalization from ethanol, the purified product melted at 244° C. CH3CN λ max 553 nm.

Workup

  1. customAfter 30 minutes at room temperature the product was precipitated by the addition of ether
  2. custompurified by chromatography on silica gel
  3. customAfter recrystalization from ethanol

Sources & evidence

ORD record
ord-13d3865f537c48a4a4becfb064f61741
Source dataset
uspto-grants-1977_06
Patent number
US04030932

Reaction notes

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