Hydrochloric Acid → HCID 54428804, compound

HRID 341735

Reaction equation

HRID 341735 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([Cl:14])[C:7]=1N.Cl.[CH3:16][S:17]SC>O.C(O)(=O)C.[Cu]>[Cl:5][C:6]1[C:7]([S:17][CH3:16])=[C:9]([Cl:14])[CH:10]=[CH:11][C:12]=1[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 1165292,6-Dichloro-3-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 54428804HCID 54428804, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (12.0 g) in water was added to a stirred suspension of 2,6-dichloro-3-methylaniline (30.0 g) in a mixture of glacial acetic acid and concentrated hydrochloric acid. While maintaining the temperature below 10° C. The mixture was stirred at 0° C. for three quarters of an hour then added to a mixture of dimethyl disulphide (20 ml) and copper powder (0.25 g) in glacial acetic acid. The mixture was stirred for 4 hours and extracted with ether. The organic layer was washed with aqueous sodium carbonate (2M), water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 2,4-dichloro-3-(methylsulphenyl)toluene (27.2 g) as a red liquid NMR (CDCl3) 2.4(s,3H), 2.45(s,3H), 7.15(d,1H), 7.3(d,1H).

Workup

  1. temperatureWhile maintaining the temperature below 10° C
  2. stirringThe mixture was stirred for 4 hours
  3. extractionextracted with ether
  4. washThe organic layer was washed with aqueous sodium carbonate (2M), water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b8985a846b5a4156bb3bc733b0afee4a
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Linked notes

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