2-(1-Imidazolyl)-2-(4-chloromethyl-1,3-dithiolan-2-ylidene)acetonitrile → 2-(1-Imidazolyl)-2-(4-methylidene-1,3-dithiolan-2-ylidene)acetonitrile

HRID 649207Notes

Reaction equation

HRID 649207 reaction equation
[N:1]1([C:6](=[C:9]2[S:13][CH:12]([CH2:14]Cl)[CH2:11][S:10]2)[C:7]#[N:8])[CH:5]=[CH:4][N:3]=[CH:2]1>O1CCCC1>[N:1]1([C:6](=[C:9]2[S:13][C:12](=[CH2:14])[CH2:11][S:10]2)[C:7]#[N:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 1

HCID 544047212-(1-Imidazolyl)-2-(4-chloromethyl-1,3-dithiolan-2-ylidene)acetonitrile

Product 1

HCID 537472672-(1-Imidazolyl)-2-(4-methylidene-1,3-dithiolan-2-ylidene)acetonitrileYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran were dissolved 0.52 g (0.002 mole) of the 2-(1-imidazolyl)-2-(4-chloromethyl-1,3-dithiolan-2-ylidene)acetonitrile obtained in Example 2 and 0.31 g of 1,8-diazabicyclo-[5,4,0]-7-undecene, and the reaction was carried out with heating under reflux for 1 hour. After the reaction solution was allowed to cool, the deposited salt was separated by filtration and the filtrate was concentrated to obtain crude crystals, which were then recrystallized from ethyl acetate-n-hexane to obtain 0.35 g of the desired compound in the form of crystals: melting point 115.7° C., yield 79%.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. customthe deposited salt was separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customto obtain crude crystals, which
  7. customwere then recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-a8fc4300b8ca4991a6c6e276d379204d
Source dataset
uspto-grants-1988_04
Patent number
US04738976

Reaction notes

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