Potassium Carbonate → HCID 66740992, compound

HRID 1627248Notes

Reaction equation

HRID 1627248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:17](=[S:26])[NH:16][N:15]=2)([CH3:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].[Cl:33][C:34]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:35]=1[CH2:36]Cl>CC(C)=O>[Cl:33][C:34]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:35]=1[CH2:36][S:26][C:17]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[C:14]([C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH3:13])[CH3:12])=[N:15][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 68087716HCID 68087716, compound

Product 1

HCID 66740992HCID 66740992, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(2-(3,4-dimethoxyphenyl)propan-2-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione (200 mg, 0.54 mmol) and K2CO3 (111 mg, 0.80 mmol) in acetone (15 mL) was stirred for 30 min at room temperature. 2-Chloro-6-fluorobenzyl chloride (206 μL, 1.61 mmol) was added to the reaction mixture, and the resulting mixture was refluxed for 2 h. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated. Purification by flash chromatography [Hex/EtOAc, 1:4 to 1:1] afforded the title product (230 mg, 0.45 mmol, 83%). 1H NMR (400 MHz, CDCl3) δ 7.20-7.12 (m, 2H), 6.95-6.91 (m, 1H), 6.84-6.80 (m, 2H), 6.68 (d, 1H), 6.54 (d, 1H), 6.50 (dd, 1H), 6.45-6.40 (m, 2H), 4.45 (s, 2H), 3.87 (s, 3H), 3.77 (s, 3H), 1.65 (s, 6H); MS (EI) m/z 516 (MH+).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. concentrationconcentrated
  5. customPurification by flash chromatography [Hex/EtOAc, 1:4 to 1:1]

Sources & evidence

ORD record
ord-0c627470ac95462c8f4cfd343fec8fd0
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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