Hydrochloric Acid → HCID 13565136, compound

HRID 1248890Notes

Reaction equation

HRID 1248890 reaction equation
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].C(N(CC)CC)C.[Cl-].C(OC(=O)O)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][C:31]2[N:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[N:32]=2)=[CH:26][CH:25]=1.Cl>O1CCCC1.O>[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([NH:23][C:24]1[CH:25]=[CH:26][C:27]([S:30][C:31]2[N:32]=[C:33]([CH3:38])[CH:34]=[C:35]([CH3:37])[N:36]=2)=[CH:28][CH:29]=1)=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27374774-[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]anilineHCID 98554652-methoxy-2-methylpropanoic acidHCID 86741142HCID 86741142, compound

Product 1

HCID 13565136HCID 13565136, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.8 g (0.1 mole) of α-methoxy-isobutyric acid were dissolved in 150 ml of tetrahydrofuran, and 10.1 g (0.1 mole) of triethylamine were added. 10.85 g (0.1 mole) of carbonic acid ethyl ester-chloride were added dropwise at 10°-15° C., with stirring. The mixture was subsequently stirred at room temperature for 2 hours and 23.1 g (0.1 mole) of 2-(4-aminophenylmercapto)-4,6-dimethyl-pyrimidine were then added in portions. The mixture was subsequently stirred at room temperature for 1 hour and boiled under reflux for a further 2 hours. The reaction mixture was cooled and then stirred into one liter of water rendered slightly acid with hydrochloric acid. The crystals precipitated were filtered off with suction, washed with water and dried in air. 27.4 g (83% of theory) of 2-(4-(α-methoxy-isobutyrylamino)-phenylmercapto)-4,6-dimethyl-pyrimidine were obtained.

Workup

  1. stirringThe mixture was subsequently stirred at room temperature for 2 hours
  2. stirringThe mixture was subsequently stirred at room temperature for 1 hour
  3. temperatureunder reflux for a further 2 hours
  4. temperatureThe reaction mixture was cooled
  5. customThe crystals precipitated
  6. filtrationwere filtered off with suction
  7. washwashed with water
  8. customdried in air

Sources & evidence

ORD record
ord-7e2552c3f6844bee940844d27853980c
Source dataset
uspto-grants-1986_12
Patent number
US04627871

Reaction notes

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