Benzoic Acid → HCID 178504832, compound

HRID 1798891Notes

Reaction equation

HRID 1798891 reaction equation
[CH2:1]([N:8]1[CH2:18][CH2:17][C:16]2[C:19]3[C:13]([NH:14][N:15]=2)=[N:12]C(SC)=[N:10][C:9]1=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.C(O)(=O)C1C=CC=CC=1.C([O-])(O)=O.[Na+].[CH3:47][S:48]([CH3:50])=[O:49]>ClCCl>[CH2:1]([N:8]1[CH2:18][CH2:17][C:16]2[C:19]3[C:13]([NH:14][N:15]=2)=[N:12][C:47]([S:48]([CH3:50])(=[O:30])=[O:49])=[N:10][C:9]1=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178503323HCID 178503323, compound

Product 1

HCID 178504832HCID 178504832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-benzyl-4-methylsulfanyl-2,6,7,8-tetrahydro-1,2,3,5,6-pentaazaacenaphthylene (2.08 g, 7.00 mmol) in anhydrous dichloromethane (100 ml) was added solid m-CPBA (4.69 g, 77% pure, 21.0 mmol) directly. The reaction became clear immediately. After stirring overnight at room temperature, a white precipitate crashed out (benzoic acid and product) from the reaction. The reaction was monitored by HPLC to ensure completion (>95%). It was noreworthy that extended reaction time led to over-oxidation and 12-15 hours seemed optimal in most cases. DMSO (50-70 ml) was added to quench the reaction and the reaction was stirred for 30 min at room temperature. aq. NaHCO3 (100 ml) was added in one shot while stirring. Some precipitates remained. The off-white precipitates were filtered washed with a lot of water to give the desired product. The dichloromethane layer was separated, washed with aq. NaCl twice and concentrated. More precipitate crashed out. The precipitates were filtered and washed with a lot of water to give the desired product as an off-white solid. Combining all products yield product in total (1.35 g, 58%). The product was further dried by high vacuum pump and was used without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 13.64 (s, 1H), 7.28-7.41 (m, 5H), 4.89 (s, 2H), 3.74 (t, J=6.4 Hz, 2H), 3.15 (t, J=6.4 Hz, 2H), 2.51 (s, 3H). LC-Mass (m/e): 330.54 (M+1).

Workup

  1. custom12-15 hours
  2. customto quench
  3. customthe reaction
  4. stirringthe reaction was stirred for 30 min at room temperature
  5. stirringwhile stirring
  6. customThe off-white precipitates
  7. filtrationwere filtered
  8. washwashed with a lot of water

Sources & evidence

ORD record
ord-3a62a81092124749950873db8cc41906
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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