1,1-Dichloroethane → HCID 18454781, compound

HRID 2369377Notes

Reaction equation

HRID 2369377 reaction equation
[Cl:1][CH:2](Cl)[CH3:3].[C:5]1([CH3:25])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[NH:13][CH:14]=[N:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24]>>[Cl-:1].[C:21]1([CH3:22])[CH:20]=[C:19]([CH3:23])[CH:18]=[C:17]([CH3:24])[C:16]=1[NH+:15]1[CH2:3][CH2:2][N:13]([C:6]2[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[CH3:25])[CH2:14]1

Participants

3

Reactant 2

HCID 63651,1-DichloroethaneHCID 3355627N,N'-dimesitylformamidine

Product 1

HCID 18454781HCID 18454781, compoundYield 49%

Conditions

Temperature
120 °C

Procedure

According to method B1, dichloroethane (1.36 mL) was added to a schlenk flask charged with N,N′-dimesitylformamidine (0.5 g, 1.78 mmol). The tube was evacuated until solvent began to bubble and then sealed and heated with stirring to 120° C. for 24 hours. The reaction mixture was then cooled, added to toluene (40 mL) and then brought to reflux. While still hot, the precipitate was collected by vacuum filtration, washed with toluene (5 mL) and dried in vacuo to afford 1,3-dimesitylimidazolinium chloride (0.3 g, 49%) as a light peach powder.

Workup

  1. additionwas added to a schlenk flask
  2. customThe tube was evacuated until solvent
  3. customto bubble
  4. customsealed
  5. temperatureheated
  6. temperatureThe reaction mixture was then cooled
  7. additionadded to toluene (40 mL)
  8. temperatureto reflux
  9. filtrationWhile still hot, the precipitate was collected by vacuum filtration
  10. washwashed with toluene (5 mL)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-d8e99c7c83cf4b52bb220bddc36af41e
Source dataset
uspto-grants-2014_04
Patent number
US08703965B2

Reaction notes

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