2-(2-Bromo-phenylsulfanyl)-5-nitro-benzenesulfinic acid → 1-Bromo-7-nitro-thianthrene

HRID 33790Notes

Reaction equation

HRID 33790 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[S:18](O)=O>CS(O)(=O)=O>[Br:1][C:2]1[C:3]2[S:8][C:9]3[C:10](=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)[S:18][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 597974372-(2-Bromo-phenylsulfanyl)-5-nitro-benzenesulfinic acid

Product 1

HCID 597974311-Bromo-7-nitro-thianthreneYield 61%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
50 °C

Procedure

2-(2-Bromo-phenylsulfanyl)-5-nitro-benzenesulfinic acid (208.5 g, 557 mmol) thinly ground was dissolved slowly in methanesulfonic acid (2 litre) with stirring. The mixture was stirred and heated at 50° C. for 17 hours. The solution was poured onto ice (5 L) with stirring, then filtered and the solid collected. The residue was suspended in water (500 ml) and then basified to pH 8 with concentrated ammonia. The solid was then filtered, suspended into methanol (1 L) and filtered again. The solid was then dried in a desiccator under vacuum to give the title compound (115 g, 61%). m/z (LC-MS, ESP), RT=5.53 min (no ionisation). 1HNMR (300 MHz, CDCl3): δH=7.15 (1H, t), 7.45 (1H, dd), 7.58 (1H, dd), 7.67 (1H, d), 8.11 (1H, dd), 8.31 (1H, d).

Workup

  1. stirringThe mixture was stirred
  2. additionThe solution was poured onto ice (5 L)
  3. stirringwith stirring
  4. filtrationfiltered
  5. customthe solid collected
  6. filtrationThe solid was then filtered
  7. filtrationfiltered again
  8. customThe solid was then dried in a desiccator under vacuum

Sources & evidence

ORD record
ord-69d6f414d90c4ac1b9a35650a68ff838
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

Loading…