Sulfuric Acid → HCID 178520209, compound

HRID 1106786

Reaction equation

HRID 1106786 reaction equation
[Cl:1][C:2]1([C:5]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1.C([Li])CCC.[S].[S:27](=O)(=O)(O)O>CCCCCC.O1CCCC1>[Cl:1][C:2]1([C:5]([OH:20])([CH2:14][N:15]2[C:19]([SH:27])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 119361alpha-(1-Chlorocyclopropyl)-alpha-((2-chlorophenyl)methyl)-1H-1,2,4-triazole-1-ethanolHCID 5362487SulfurHCID 178418339Butyllithium

Product 1

HCID 178520209HCID 178520209, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

At -20° C., a mixture of 3.12 g (10 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol and 45 ml of absolute tetrahydrofuran is admixed with 8.4 ml (21 mmol) of n-butyllithium in hexane and stirred at 0° C. for 30 minutes. The reaction mixture is then cooled to -70° C., admixed with 0.32 g (10 mmol) of sulphur powder and stirred at -70° C. for 30 minutes. The mixture is warmed to -10° C., admixed with ice-water and adjusted to pH 5 by addition of dilute sulphuric acid. The mixture is extracted repeatedly with ethyl acetate and the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. In this manner, 3.2 g (93% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of a solid substance which, after recrystallization, melts at 138-139° C.

Workup

  1. temperatureThe reaction mixture is then cooled to -70° C.
  2. stirringstirred at -70° C. for 30 minutes
  3. temperatureThe mixture is warmed to -10° C.
  4. extractionThe mixture is extracted repeatedly with ethyl acetate
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2caf5cbefd3844d9b722fa231dbb8fc8
Source dataset
uspto-grants-2000_05
Patent number
US06057353

Linked notes

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