Triethylamine → HCID 86737270, compound

HRID 903556Notes

Reaction equation

HRID 903556 reaction equation
C(N([CH2:6][CH3:7])CC)C.[CH3:8][C:9]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:10]=1[O:11][CH2:12][C:13]1[NH:14][CH2:15][CH2:16][N:17]=1.S(Cl)Cl>C(Cl)Cl.O>[CH3:8][C:9]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:10]=1[O:11][CH2:12][C:13]1[N:17]([CH2:12][O:11][C:10]2[CH:9]=[CH:21][CH:20]=[C:19]([CH3:18])[C:6]=2[CH3:7])[CH2:16][CH2:15][N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25353Sulfur dichlorideHCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole

Product 1

HCID 86737270HCID 86737270, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

11 g of triethylamine are added slowly dropwise at 0° C. to a solution of 20.4 g of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline in 200 ml of methylene chloride, followed by the slow dropwise addition of 5.15 g of freshly distilled sulfur chloride. The reaction mixture is then stirred for about 2 hours in an ice bath, the resultant solution is diluted with water and the organic phase is washed repeatedly with water, dried over sodium sulfate and concentrated completely. The residue is stirred in hexane and recrystallisation of the solid precipitate yields bis-(2,3-dimethylphenoxymethyl)-2-imidazoline)-1,1'-sulfide (compound 1) of the formula ##STR5## in the form of a light beige-coloured powder with a melting point of 112°-114° C.

Workup

  1. washthe organic phase is washed repeatedly with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated completely
  4. stirringThe residue is stirred in hexane
  5. customrecrystallisation of the solid precipitate

Sources & evidence

ORD record
ord-92ff54093c614804963f9c6870d95bd7
Source dataset
uspto-grants-1980_10
Patent number
US04228175

Reaction notes

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