Sodium Chloride → HCID 13644551, compound

HRID 2119160Notes

Reaction equation

HRID 2119160 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[N:10][CH:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])[CH3:4].[CH:25]1([CH2:28][OH:29])[CH2:27][CH2:26]1.Cl[C:31](OC(Cl)(Cl)Cl)=[O:32].[Na+].[Cl-]>O1CCCC1>[CH:25]1([CH2:28][O:29][C:31]([N:10]2[CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])=[C:13]([CH3:14])[N:12]=[C:11]2[CH3:15])=[O:32])[CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 10426DiphosgeneHCID 24758Sodium hydride2×HCID 75644CyclopropanemethanolHCID 20191108HCID 20191108, compound

Product 1

HCID 13644551HCID 13644551, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

On the other hand, 45 mg of 50% suspension of sodium hydride (0.94 millimole) in oil was suspended in 3 ml of anhydrous tetrahydrofuran. To the suspension 259 mg (0.85 millimole) of 5-ethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)dihydropyrimidine in 5 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred for further 5 minutes. To the solution the above reaction mixture of the above sodium hydride, cyclopropylcarbinol and trichloromethyl chloroformate was added at 0° C. After 15 minutes, saturated NaCl solution was added to the mixture and it was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified on silica gel by thin layer chromatography (developer: chloroform/methanol 10:1) to obtain 122 mg (36% yield) of title compound.

Workup

  1. stirringThe mixture was stirred for further 5 minutes
  2. additionwas added at 0° C
  3. extractionwas extracted with chloroform
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel by thin layer chromatography (developer: chloroform/methanol 10:1)

Sources & evidence

ORD record
ord-fe6ee61928e145a4b6533482f28f9537
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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