Triethylamine → HCID 178441983, compound

HRID 2050886Notes

Reaction equation

HRID 2050886 reaction equation
Br.Br.[C:3]([C:7]1[N:11]=[C:10]([S:12][CH2:13][CH2:14][NH2:15])[NH:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C(Cl)Cl>[C:3]([C:7]1[N:11]=[C:10]([S:12][CH2:13][CH2:14][NH:15][C:32](=[O:33])[NH:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:35])[F:34])=[CH:26][CH:27]=2)[NH:9][N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178419251HCID 178419251, compound

Product 1

HCID 178441983HCID 178441983, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

To 10 g (27 mmole) of 3-t-butyl-5-(2-aminoethylthio)-1H-1,2,4-triazole dihydrobromide in 100 ml of methylene chloride was added 5.5 g (54 mmole) of triethylamine. The mixture was cooled to -40° C. and a solution of 5.2 g (27 mmole) of 4-trifluoromethylphenyl isocyanate in methylene chloride was slowly added. The stirred mixture was slowly allowed to warm to room temperature and was stirred at room temperature for eighteen hours. The reaction mixture was washed twice with water, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 9 g of 3-t-butyl-5-(2-(4-trifluoromethylphenylcarbamoylamino)-ethylthio)-1H-1,2,4-triazole, m.p. 238°-240° C.

Workup

  1. temperatureto warm to room temperature
  2. washThe reaction mixture was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45ac440a9ec74d749ca6640b4f9ca689
Source dataset
uspto-grants-1991_05
Patent number
US05015652

Reaction notes

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