2,3-Dimethylaniline → HCID 53746487, compound

HRID 1283085Notes

Reaction equation

HRID 1283085 reaction equation
Cl[CH:2]1[N:7](Cl)[CH:6]=[CH:5][C:4]([Cl:9])=[N:3]1.C(=O)([O-])[O-].[Na+].[Na+].[SH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH3:23][C:24]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26]>C(O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][S:16][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([NH:26][C:25]2[CH:27]=[CH:28][CH:29]=[C:30]([CH3:31])[C:24]=2[CH3:23])[N:7]=1)[CH3:22]

Participants

6

Reactant 4

HCID 68932,3-DimethylanilineHCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 21519304HCID 21519304, compound

Product 1

HCID 53746487HCID 53746487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18.3 g. of 2,3,6-trichloropyrimidine, 10.6 g. of sodium carbonate and 12.0 g. of ethyl mercaptoacetate in 250 ml. of ethanol was heated with stirring under reflux for 3 hours. 2,3-Dimethylaniline (12.2 g.) was added and refluxing with stirring was continued overnight. The reaction mixture was filtered and the filtrate taken to dryness on a rotary evaporator. The residual oil was dissolved in 100 ml. of ethyl acetate and the resulting solution was diluted to 250 ml. with petroleum ether. There was obtained 5 g. of product. Recrystallization from heptane gave 3.8 g. of pure product, mp. 114°-116°C.

Workup

  1. additionA mixture of 18.3 g
  2. temperatureunder reflux for 3 hours
  3. temperaturerefluxing
  4. stirringwith stirring
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate taken to dryness on a rotary evaporator
  7. dissolutionThe residual oil was dissolved in 100 ml
  8. additionof ethyl acetate and the resulting solution was diluted to 250 ml
  9. customThere was obtained 5 g
  10. customRecrystallization from heptane
  11. customgave 3.8 g

Sources & evidence

ORD record
ord-6d256c05aa264312bba8b813cd2b4821
Source dataset
uspto-grants-1976_08
Patent number
US03974162

Reaction notes

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