Dichlone → HCID 67331251, compound

HRID 1186652Notes

Reaction equation

HRID 1186652 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:19][C:20]1[C:21](=[O:32])[C:22]2[C:27]([C:28](=[O:31])[C:29]=1Cl)=[CH:26][CH:25]=[CH:24][CH:23]=2>CCO>[Cl:19][C:20]1[C:21](=[O:32])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28](=[O:31])[C:29]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8342DichloneHCID 5935694-Amino-N-(2-methylphenyl)benzenesulfonamide

Product 1

HCID 67331251HCID 67331251, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

A well-stirred suspension of 4-Amino-N-o-tolyl-benzenesulfonamide 12a (47 mg, 179 mmol) and 2,3-dichloro-1,4-naphthquinone (41 mg, 179 mmol) in 10.0 mL of 95% EtOH/5% water solution mixture was refluxed at 115° C. for three days. The orange precipitate obtained was filtered and washed with hot ethanol (5×5 mL), dried under reduced pressure to afford the title compound (23 mg, 28%). Mp=265-266° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.55 (br s, 1H), 9.45 (br s, 1H), 8.04 (d, J=7.2 Hz, 2H), 7.89-7.80 (m, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.17-7.07 (m, 5H), 6.98-6.96 (m, 1H), 1.97 (s, 3H); ESI-LRMS m/z 453.0 (M+35Cl+H)+, 455.0 (M+37Cl+H)+; ESI-HRMS m/z calculated for C23H8ClN2O4S (M+H)+ 453.0670, found 453.0665.

Workup

  1. customThe orange precipitate obtained
  2. filtrationwas filtered
  3. washwashed with hot ethanol (5×5 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b024b65fb84c4980b31c925581df27bf
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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