Dimethylformamide → HCID 57811504, compound

HRID 660429Notes

Reaction equation

HRID 660429 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]1[CH:24]=[C:23]([CH3:25])[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]=1[N:26]1[C:30]([C:31]([F:34])([F:33])[F:32])=[N:29][N:28]=[C:27]1[SH:35].CN(C=O)C>C1COCC1.O>[CH3:14][C:15]1[CH:24]=[C:23]([CH3:25])[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]=1[N:26]1[C:30]([C:31]([F:34])([F:33])[F:32])=[N:29][N:28]=[C:27]1[S:35][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetate2×HCID 11430Potassium CarbonateHCID 178425472HCID 178425472, compound

Product 1

HCID 57811504HCID 57811504, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-bromoacetate (68 μL, 0.611 mmol) and potassium carbonate (0.17 g, 1.22 mmol) were added to a solution of 4-(2,4-Dimethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazole-3-thiol (0.2 g, 0.611 mmol) in THF (2.44 mL). The resulting mixture was heated at 60° C. for 18 hours. The mixture was concentrated, ethyl 2-bromoacetate (68 μL, 0.611 mmol) and DMF (1.2 mL) added, and the mixture heated at 60° C. for 24 hours. Water (40 mL) was added and the mixture extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by SGC (0-50% ethyl acetate/Hexanes) to afford ethyl 2-(4-(2,4-dimethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-ylthio)acetate as a clear oil (0.137 g, 54%).

Workup

  1. concentrationThe mixture was concentrated
  2. temperaturethe mixture heated at 60° C. for 24 hours
  3. extractionthe mixture extracted with ethyl acetate (2×40 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by SGC (0-50% ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-0fa2c27b4a724b949838b8f8e9b59546
Source dataset
uspto-grants-2011_12
Patent number
US08084483B2

Reaction notes

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