Sulfuric Acid → HCID 15132837, compound

HRID 1288710Notes

Reaction equation

HRID 1288710 reaction equation
N([O-])=O.[Na+].[CH3:5][O:6][C:7]([C:9]1[C:10]([CH3:20])=[C:11]([CH:15]=[CH:16][C:17]=1[S:18][CH3:19])[C:12](N)=[O:13])=[O:8].S(=O)(=O)(O)[OH:22]>O.C(O)(=O)C>[CH3:5][O:6][C:7]([C:9]1[C:10]([CH3:20])=[C:11]([CH:15]=[CH:16][C:17]=1[S:18][CH3:19])[C:12]([OH:22])=[O:13])=[O:8]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 53697072HCID 53697072, compound

Product 1

HCID 15132837HCID 15132837, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Sodium nitrite (2.4 g) was added dropwise to a stirred solution of 3-methoxycarbonyl-2-methyl-4-methylsulphenylbenzamide (4.2 g) in a mixture of concentrated sulphuric acid (50 ml), water (40 ml) and glacial acetic acid (70 ml) whilst maintaining the temperature below 5° C. The mixture was stirred without cooling for 0.5 hours. The brown solution was recooled to 0° C. and water (200 ml) was added. The mixture was extracted with ether (3×150 ml). The combined organic extracts were washed with water (2×150 ml), dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 3-methoxycarbonyl-2-methyl-4-methylsulphenylbenzoic acid (4.6 g) as a sticky orange solid NMR (CDCl3) 2.1(s,3H), 2.5(s,3H), 3.9(s,3H), 7.0(d,1H), 7.85(d,1H), 9.0(bs, 1H).

Workup

  1. temperaturewhilst maintaining the temperature below 5° C
  2. temperaturewithout cooling for 0.5 hours
  3. customwas recooled to 0° C.
  4. extractionThe mixture was extracted with ether (3×150 ml)
  5. washThe combined organic extracts were washed with water (2×150 ml)
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-be3109ce1d804fb4934b9c9cf24eadaf
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

Loading…