O-Toluidine → HCID 13057309, compound

HRID 1758908Notes

Reaction equation

HRID 1758908 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:18][C:19]#[N:20].[NH4+].[CH3:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>CCCCCC.O.C(Cl)(Cl)Cl>[C:1]([C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:20][C:19]([NH:25][C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[CH3:22])=[S:18])=[O:6])([O:12][CH3:13])=[O:11]

Participants

8

Reactant 4

HCID 7242O-ToluidineHCID 15666Ammonium thiocyanateHCID 20392Monomethyl phthalateHCID 24386Thionyl Chloride

Product 1

HCID 13057309HCID 13057309, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

To a 25 ml of dry chloroform, 5.4 g (0.03 m) methyl hydrogen phthalate and 3.9 g (0.033 m) thionyl chloride is added. Stir and reflux for 3 hours and cool to room temperature. To this solution 2.3 g (0.03 m) ammonium thiocyanate is added and the mixture is stirred for 3 hours at room temperature until it changed to bellow. Finally, 3.2 g (0.03 m) 2-methylaniline is added and stirred at room temperature overnight. The mixture is added to water and then some hexane is added to give fine precipitates. Filter, wash with water, hexane and dry to give 6.1 g, desired product, m.p. 143-45, yield 62%.

Workup

  1. temperaturereflux for 3 hours
  2. stirringthe mixture is stirred for 3 hours at room temperature until it
  3. stirringstirred at room temperature overnight
  4. customto give fine precipitates
  5. filtrationFilter
  6. washwash with water, hexane
  7. customdry

Sources & evidence

ORD record
ord-8878f61460314fa888cf638829d07943
Source dataset
uspto-grants-1982_07
Patent number
US04338257

Reaction notes

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