Dichloromethane → 2-((2,4-Dichloroanilino)methyl)-2-imidazoline

HRID 66762Notes

Reaction equation

HRID 66762 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:14]=1[NH:15][CH2:16][C:17]1[NH:18][CH2:19][CH2:20][N:21]=1.C(Cl)Cl>O>[Cl:12][C:13]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:14]=1[NH:15][CH2:16][C:17]1[NH:21][CH2:20][CH2:19][N:18]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 205290662-((2,4-Dichloroanilino)methyl)-2-imidazoline p-toluenesulfonate

Product 1

HCID 205290672-((2,4-Dichloroanilino)methyl)-2-imidazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.5 grams (g) of 2,4-dichloroanilinoacetonitrile, 23.3 g of ethylenediamine p-toluenesulfonate and 75 milliliters (ml) of 1,2-dichlorobenzene was heated with stirring in a round-bottomed three-necked flask at from about 140°-170° C. for about 70 minutes under a small flow of nitrogen. The reaction mixture was cooled and then diluted with methylene chloride. The mixture was cooled and then filtered, which gave 35.1 g of 2-((2,4-dichloroanilino)methyl)-2-imidazoline p-toluenesulfonate as white crystals. The p-toluenesulfonate salt was slurried in water and CH2Cl2 and then basified. The CH2Cl2 layer was separated and the remaining aqueous portion extracted with CH2Cl2 and then CHCl3. The extracts were combined, treated with diatomaceous earth and activated charcoal, and then filtered. Concentrating the filtrate to dryness, left 17.0 g of crystals. Recrystallization from ethylene dichloride gave 14.0 g of purified 2-((2,4-dichloroanilino)methyl)-2-imidazoline as white crystals, having a melting point (m.p.) of 154°-156° C.

Workup

  1. customThe CH2Cl2 layer was separated
  2. extractionthe remaining aqueous portion extracted with CH2Cl2
  3. additiontreated with diatomaceous earth and activated charcoal
  4. filtrationfiltered
  5. concentrationConcentrating the filtrate to dryness
  6. waitleft 17.0 g of crystals
  7. customRecrystallization from ethylene dichloride

Sources & evidence

ORD record
ord-319ebae7e3ee41ed996af7686be1c5bb
Source dataset
uspto-grants-1982_08
Patent number
US04343810

Reaction notes

Loading…