Potassium Carbonate → 4-(2,5-Dichlorophenylthio)-3-nitrobenzonitrile

HRID 1946840Notes

Reaction equation

HRID 1946840 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[SH:21].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[S:21][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 799652,5-Dichlorobenzenethiol

Product 1

HCID 595489374-(2,5-Dichlorophenylthio)-3-nitrobenzonitrileYield 300.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzonitrile (10.0 g, 54.77 mmol) in THF (300 mL) was added 2,5-dichlorobenzenethiol (19.6 g, 12.108 mmol) and K2CO3 (37.8 g, 273.85 mmol). The reaction mixture was refluxed for 48 hrs. The solid was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated NaHCO3, H2O, and saturated NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo. The resulting solid was then triturated with DCM and hexanes, and filtered to yield compound 27 as a yellow solid (11.823 g, 91.0% HPLC purity, 66.4% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.82 (d, J=2 Hz, 1H), 8.00 (m, 3H), 7.80 (d, J=9 Hz, 1H), 7.75 (dd, J1=3 Hz, J2=9 Hz, 1H), 6.97 (d, J=9 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. filtrationThe solid was filtered
  3. washwashed with copious amounts of EtOAc
  4. washThe filtrate was washed sequentially with saturated NaHCO3, H2O, and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting solid was then triturated with DCM and hexanes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-01a897dc2e8a49a9b0cb49e35088516d
Source dataset
uspto-grants-2013_03
Patent number
US08399456B2

Reaction notes

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