5-Chloro-2-methylaniline → HCID 54254977, compound

HRID 2256949Notes

Reaction equation

HRID 2256949 reaction equation
N(OC(C)(C)C)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([CH:15]=1)N.[CH3:17][S:18]SC>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([S:18][CH3:17])[CH:15]=1

Participants

5

Reactant 3

HCID 72605-Chloro-2-methylaniline2×HCID 10906Tert-Butyl nitrite2×HCID 12232Dimethyl Disulfide

Product 1

HCID 54254977HCID 54254977, compoundYield 504.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-Butyl nitrite (4 ml) was added to a mixture of 5-chloro-2-methylaniline (4 g) and dimethyl disulphide (26.3 g) in chloroform. After the reaction started t-butyl nitrite (17.7 ml) and 5-chloro-2-methylaniline (16 g) were added simultaneously. The mixture was stirred at room temperature for 2 hours and left to stand overnight. The mixture was washed with water, aqueous hydrochloric acid (2M), water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 4-chloro-2-methylsulphenyltoluene (24.6 g) as a red oil, NMR (CDCl3): 2.2(s,3H), 2.4(s,3H), 6.85(s,2H), 7.0(s, 1H).

Workup

  1. additionwere added simultaneously
  2. waitleft
  3. waitto stand overnight
  4. washThe mixture was washed with water, aqueous hydrochloric acid (2M), water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-70bda44ed97f4b87b592a68859656c76
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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