1,1-Dichloroethane → HCID 18454781, compound

HRID 2369376Notes

Reaction equation

HRID 2369376 reaction equation
[CH:1](N(C(C)C)CC)(C)[CH3:2].[C:10]1([CH3:30])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[NH:18][CH:19]=[N:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=1[CH3:29].[Cl:31]C(Cl)C>>[Cl-:31].[C:26]1([CH3:27])[CH:25]=[C:24]([CH3:28])[CH:23]=[C:22]([CH3:29])[C:21]=1[NH+:20]1[CH2:2][CH2:1][N:18]([C:11]2[C:12]([CH3:17])=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=2[CH3:30])[CH2:19]1

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 81531DiisopropylethylamineHCID 3355627N,N'-dimesitylformamidine

Product 1

HCID 18454781HCID 18454781, compoundYield 92%

Conditions

Temperature
120 °C

Procedure

According to method A1, diisopropylethylamine (0.34 mL, 1.96 mmol) was added to a stirred solution of N,N′-dimesitylformamidine (0.5 g, 1.78 mmol) and dichloroethane (1.36 mL, 17.8 mmol) in a schlenk tube. The tube was evacuated until solvent began to bubble and then sealed and heated 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 (0.56 g, 92%) as a light peach powder.

Workup

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

Sources & evidence

ORD record
ord-ac2fafc0fd304b279521f6eebcdf6f35
Source dataset
uspto-grants-2014_04
Patent number
US08703965B2

Reaction notes

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