Triethylamine → HCID 12919006, compound

HRID 903155Notes

Reaction equation

HRID 903155 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[S:4].[CH3:7][C:8]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:7][C:8]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][C:12]1[N:16]([C:3](=[S:4])[N:2]([CH3:6])[CH3:1])[CH2:15][CH2:14][N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole

Product 1

HCID 12919006HCID 12919006, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of dimethylthiocarbamoyl chloride (2.47 g; 0.020 mole) in chloroform (10 ml) was added dropwise during 10 minutes, to a stirred solution of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline (4.08 g; 0.020 mole) prepared as in Example 1--and triethylamine (2.0 g; 0.20 mole) in chloroform (50 ml) cooling to keep the reaction below 5° C. The reaction temperature was then allowed to rise to room temperature and finally the reaction was refluxed for 5 hours. After cooling the reaction mixture was washed with water, dried and evaporated. The residue was recrystallised from isopropanol to yield white crystals of 2-(2,3-dimethylphenoxymethyl)-1-(N,N-dimethylthiocarbamoyl)-2-imidazoline, m.p. 124°-127° C. Analysis: Calculated C 61.84, H 7.27, N 14.42%. Found: C 62.15, H 7.64, N 14.35%.

Workup

  1. customthe reaction below 5° C
  2. customto rise to room temperature
  3. temperaturefinally the reaction was refluxed for 5 hours
  4. temperatureAfter cooling the reaction mixture
  5. washwas washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-fd774cc0896440db8cc9608e5bce192b
Source dataset
uspto-grants-1980_10
Patent number
US04226876

Reaction notes

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