Hydrochloric Acid → HCID 54725927, compound

HRID 225342Notes

Reaction equation

HRID 225342 reaction equation
[O-]CC.[Na+].[C:5]([O:13]CC)(=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:16][S:17][C:18]1[N:19]=[CH:20][C:21]2[C:26](=O)[O:25]C(=O)[N:23]([CH2:29][C:30]3[CH:38]=[CH:37][C:36]4[O:35][CH2:34][O:33][C:32]=4[CH:31]=3)[C:22]=2[N:39]=1.Cl>O>[CH2:10]([O:9][C:7]([C:6]1[C:5](=[O:13])[N:23]([CH2:29][C:30]2[CH:38]=[CH:37][C:36]3[O:35][CH2:34][O:33][C:32]=3[CH:31]=2)[C:22]2[N:39]=[C:18]([S:17][CH3:16])[N:19]=[CH:20][C:21]=2[C:26]=1[OH:25])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 20562028HCID 20562028, compound

Product 1

HCID 54725927HCID 54725927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide (1.6 g., 0.03 g. atom of sodium in 50 ml. of absolute ethanol) was added 4.8 g. (0.03 mole) of diethyl malonate. The ethanol was removed under suction in a rotary evaporator. To the residue was added 50 ml. of dry dimethyl formamide followed by 3.5 g. (0.01 mole) of 7-methylthio-1-piperonyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione. The reaction mixture was heated under reflux for 2 hours, cooled in ice and poured into 400 ml. of water. The reaction mixture was acidified with conc. hydrochloric acid. The resulting precipitateable amounted to 5.0 g.--m.p. 173°-178° C. Recrystallization from dimethyl formamide gave 3.4 g. of pure product--m.p. 187°-188° C.

Workup

  1. customThe ethanol was removed under suction in a rotary evaporator
  2. additionTo the residue was added 50 ml
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 2 hours
  5. temperaturecooled in ice
  6. additionpoured into 400 ml
  7. customRecrystallization from dimethyl formamide
  8. customgave 3.4 g

Sources & evidence

ORD record
ord-64d2dff5110342188b91e9ed83b8222e
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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