Hydrochloric Acid → 4-Methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine

HRID 1780580Notes

Reaction equation

HRID 1780580 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)=O.Cl>C(O)(=O)C>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]([NH2:5])=[C:7]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 190470412,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

Product 1

HCID 190470374-Methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamineYield 35.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

24 g 2,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide was dissolved in 120 mL glacial acetic acid and the mixture warmed to reflux when 60 mL 15% hydrochloric acid solution was gradually added. After the addition was completed, the reaction mixture was heated at reflux for 4 h. After cooling, volatiles were removed in vacuo, the residue was taken up in 200 mL water and ice was added. The resulting mixture was neutralized to pH 10 with 5% sodium hydroxide solution and extracted with ether. Organic extracts were washed with brine, dried, evaporated to dryness and then dried in a vacuum oven to yield 6.2 g of the title compound as a tan solid melting at 120°-123° C. 1H NMR (CDCl3): δ 2.30 (s,3H), 2.60 (s,3H), 5.8 (s,2H,NH2), 6.60-8.6 (5H).

Workup

  1. temperaturethe mixture warmed
  2. additionwas gradually added
  3. additionAfter the addition
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 4 h
  6. temperatureAfter cooling
  7. customvolatiles were removed in vacuo
  8. additionice was added
  9. extractionextracted with ether
  10. washOrganic extracts were washed with brine
  11. customdried
  12. customevaporated to dryness
  13. customdried in a vacuum oven

Sources & evidence

ORD record
ord-edd04af762124a23a9480dd065b96e68
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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