Triethylamine → HCID 53771859, compound

HRID 224526Notes

Reaction equation

HRID 224526 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[NH:5][C:6]=1[Cl:7].C(N(CC)CC)C.[C:19]1([O:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[C:19]1([O:25][C:26]([N:5]2[C:6]([Cl:7])=[C:2]([Cl:1])[N:3]=[C:4]2[C:8]([F:11])([F:10])[F:9])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 609321HCID 609321, compound

Product 1

HCID 53771859HCID 53771859, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20.5 g (0.1 mol) of 4,5-dichloro-2-trifluoromethylimidazole were dissolved in 150 ml of dioxane. 10.1 g (0.1 mol) of triethylamine were added thereto and 16.05 g (0.1 mol) of chloroformic acid phenyl ester were then added dropwise whilst cooling at 10°-15° C. The mixture was stirred for a further 2 hours at room temperature, the triethylamine hydrochloride which had separated out was filtered off and the filtrate was evaporated in vacuo. The oily residue was distilled. The main fraction boiled at 106.5°-107° C./0.08 mm Hg. 28.6 g (88% of theory) of 4,5-dichloro-2-trifluoromethyl-imidazole-1-carboxylic acid phenyl ester were obtained.

Workup

  1. temperaturewhilst cooling at 10°-15° C
  2. customthe triethylamine hydrochloride which had separated out
  3. filtrationwas filtered off
  4. customthe filtrate was evaporated in vacuo
  5. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-b28fc05b5cbd4445914ab35ce1126491
Source dataset
uspto-grants-1980_11
Patent number
US04233058

Reaction notes

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