m-Toluidine → HCID 19860393, compound

HRID 1721869Notes

Reaction equation

HRID 1721869 reaction equation
Cl[C:2]1[C:7]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]([N:16]=CN(C)C)[N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=1>CCO>[NH2:16][C:4]1[N:3]=[C:2]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[C:7]([S:8]([NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])(=[O:9])=[O:10])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 53908445HCID 53908445, compound

Product 1

HCID 19860393HCID 19860393, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-chloro-2-[[(dimethylamino)methylene]amino]-N-(1,1-dimethylethyl)-5-pyrimidinesulfonamide, prepared according to the process of Example 1, Step 6 (44.62 g, 0.139 mol) in EtOH (1800 mL) was added metatoluidine (59.8 g, 0.558 mol) and heated to reflux for 10 hours. After cooling, the solvent was removed in vacuo and the residue extracted into EtOAc (1 liter). The solution was twice washed with 1N HCl, washed with water and then with saturated NaCl. The organics were dried over MgSO4 and evaporated in vacuo to give a colorless solid, m.p. 174°-178° C. in 85% yield. Used without further purification.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureto reflux for 10 hours
  4. temperatureAfter cooling
  5. customthe solvent was removed in vacuo
  6. extractionthe residue extracted into EtOAc (1 liter)
  7. washThe solution was twice washed with 1N HCl
  8. washwashed with water
  9. dry with materialThe organics were dried over MgSO4
  10. customevaporated in vacuo
  11. customto give a colorless solid, m.p. 174°-178° C. in 85% yield
  12. customUsed without further purification

Sources & evidence

ORD record
ord-a191c09e1c30474fa5fd428ef0439764
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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