Sulfuric Acid → HCID 11673059, compound

HRID 645946Notes

Reaction equation

HRID 645946 reaction equation
C(NC(=S)[SH-][C:11]1[C:12](=O)[C:13]2[C:18]([C:19](=O)[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)C1C=CC=CC=1.Cl.[CH2:25]([NH2:32])[C:26]1C=CC=CC=1.CC[N:35]([CH2:38]C)CC.C(=S)=[S:41].C1(=O)C2C(=CC=CC=2)C(=O)C=C1.OS(O)(=O)=O>C(Cl)Cl>[NH:35]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]([CH2:20][C:11]2[N:32]=[C:25]([CH3:26])[S:41][CH:12]=2)=[CH:38]1

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 85301,4-NaphthoquinoneHCID 2724127Benzylammonium chlorideHCID 178516662HCID 178516662, compound

Product 1

HCID 11673059HCID 11673059, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-S-(naphthoquinon-2-yl)-dithiocarbamate) (32). To a suspension of benzylamine hydrochloride (300 mg, 1.87 mmoles) in CH2Cl2 (5 mL) at 0° C. was added NEt3 (208.4 mg, 2.05 mmoles) and the reaction mixture was stirred for 15 minutes followed by the addition of CS2 (142.5 mg, 1.87 mmoles). After 30 minutes, 1,4-naphthoquinone (296.1 mg, 1.87 mmoles) was added and the reaction was allowed to slowly warm to rt overnight. The reaction was poured into 1 M H2SO4 and extracted with EtOAc (3×50 mL). The organic layer was washed with brine, dried with Na2SO4, and filtered. Concentration afforded a crude product that was chromatographed (CHCl3/EtOAc/Hexanes, 1:1:2) to afford a brick red solid (125 mg, 20% yield).

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationConcentration
  7. customafforded a crude product that
  8. customwas chromatographed (CHCl3/EtOAc/Hexanes, 1:1:2)

Sources & evidence

ORD record
ord-61d282101106458f91f5ec00ea47828c
Source dataset
uspto-grants-2010_04
Patent number
US07705022B2

Reaction notes

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