O-Phenylenediamine → HCID 86671377, compound

HRID 389294Notes

Reaction equation

HRID 389294 reaction equation
O[CH:2]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]2[S:10][C:11](=[S:13])[S:12][C:4]=2[C:3]1=O.[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]>C(Cl)Cl>[OH:7][C:6]([C:5]1[S:10][C:11](=[S:13])[S:12][C:4]=1[C:3]1[CH:2]=[N:22][C:15]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:21]=1)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 66562917HCID 66562917, compound

Product 1

HCID 86671377HCID 86671377, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxy-4,4-dimethyl-2-thioxo-4H-[1,3]dithiolo[4,5-c]pyran-7(6H)-one 6 (101.0 mg, 0.41 mmol) in CH2Cl2 (15 mL), 136.6 mg (1.26 mmol) of o-phenylenediamine was added, the resulting solution was refluxed for 1 hour. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by radial chromatography using CH2Cl2 as a mobile phase that yielded 4-(2-hydroxypropan-2-yl)-5-(quinoxalin-2-yl)-1,3-dithiole-2-thione 9 as a yellow-orange solid (119.6 mg, 0.37 mmol, 92.0%). 1H NMR in CDCl3 (δ, ppm): 9.01 (1H, s), 8.18 (1H, m, ArH), 8.07 (1H, m, ArH), 7.89 (2H, m, ArH), 1.59 (6H, s, CH3); 13C NMR in CDCl3 (δ, ppm): 207.8, 158.0, 145.1, 144.3, 141.9, 140.0, 133.81, 132.3, 131.9, 129.8, 128.7, 72.3, 31.0; IR (neat, cm−1): 3199, 3007, 2962, 2917, 1531, 1045, 759, 571, 457; HR APCIMS+ (m/z): 321.0179 (M+, C14H12N2OS3, 321.0185).

Workup

  1. temperaturethe resulting solution was refluxed for 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by radial chromatography

Sources & evidence

ORD record
ord-61b2c0040ec4440ea87214ffa04ef29b
Source dataset
uspto-grants-2013_02
Patent number
US08378123B2

Reaction notes

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