Water → HCID 178468144, compound

HRID 1471942Notes

Reaction equation

HRID 1471942 reaction equation
[C:1]1([C:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[S:18])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][O:22][CH2:23][CH3:24].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:21]([O:22][CH2:23][CH2:24][S:18][C:10]1[NH:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 86657576HCID 86657576, compound

Product 1

HCID 178468144HCID 178468144, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-diphenyl-1H-pyrazole-5(4H)-thione (0.5 g, 1.981 mmol) in DMF (5 mL), were added 1-bromo-2-ethoxyethane (0.303 g, 1.981 mmol) and K2CO3 (0.274 g, 1.981 mmol) at room temperature. After stirring for 4 h, the reaction was poured into water and extracted with ethyl acetate, which was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography to give the title compound (0.45 g). LCMS m/z=343.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.1 Hz, 3H), 3.25 (m, 2H), 3.45 (m, 2H), 4.25 (q, J=7.1 Hz, 2H), 7.25-7.56 (m, 10H), 13.0 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate, which
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a56d27234cf84ab283dc85d34f85a20d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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