Hydrochloric Acid → HCID 54725927, compound

HRID 127386Notes

Reaction equation

HRID 127386 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 l 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-482125a41bc94087b906ea7dc0108e32
Source dataset
uspto-grants-1981_03
Patent number
US04255568

Reaction notes

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