P-Phenylenediamine → 4-(3-(4-Aminophenyl)thioureido)benzenesulfonamide

HRID 333127Notes

Reaction equation

HRID 333127 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N:9]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[C:10]=[S:11]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:10](=[S:11])[NH:9][C:12]2[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 5213594-Isothiocyanatobenzenesulfonamide

Product 1

HCID 577735954-(3-(4-Aminophenyl)thioureido)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,4-diaminobenzene (0.324 g, 3.0 mmol) in acetonitrile was added 4-isothiocyanatobenzenesulfonamide (0.642 g, 3.0 mmol). The mixture was stirred at room temperature for 3 h. The reaction mixture went clear and a white precipitate formed. The solid was filtered, washed with acetonitrile and dried to afford 4-(3-(4-aminophenyl)thioureido)-benzenesulfonamide as a white sold (0.829 g, 86%). 1H NMR (400 MHz, DMSO) δ 9.65 (s, 2H), 7.71 (d, J=8.8 Hz, 2H), 7.66 (d, J=8.8 Hz, 2H), 7.26 (s, 2H), 7.00 (d, J=8.4 Hz, 2H), 6.52 (d, J=6.8 Hz, 2H), 5.08 (s, 2H); MS (ESI), 323 (M+H)+.

Workup

  1. customa white precipitate formed
  2. filtrationThe solid was filtered
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-a20f5c0a2a344ff1bd5657b59d3287b6
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

Loading…