Ethyl chloroformate → HCID 13689592, compound

HRID 2119164Notes

Reaction equation

HRID 2119164 reaction equation
[CH3:1][CH:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[C:5]([C:17]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)=[O:18])=[C:4]([CH3:24])[NH:3]1.[H-].[Na+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1.[Na+].[Cl-]>[CH3:1][C:2]1[N:7]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[C:5]([C:17]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)=[O:18])=[C:4]([CH3:24])[N:3]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 20191100HCID 20191100, compound

Product 1

HCID 13689592HCID 13689592, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

270 mg (0.82 millimole) of 2,6-Dimethyl-5-cyclopropylmethoxycarbonyl-4-(2-nitrophenyl)-dihydropyrimidine in 4 ml of anhydrous tetrahydrofuran was added to 47 mg (0.98 millimole) of sodium hydride as 50% suspension in oil and stirred at room temperature for 5 minutes. Ethyl chloroformate (120 μl), 1.32 millimole) was added and stirred at room temperature for 30 minutes. The reaction solution was diluted with saturated aqueous NaCl solution and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The residue was purified on silica gel by thin layer chromatography (developer:chloroform/acetone 10:1, eluant : chloroform/methanol 4:1) to obtain 196 mg (yield 60%) of title compound.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified on silica gel by thin layer chromatography (developer:chloroform/acetone 10:1, eluant : chloroform/methanol 4:1)

Sources & evidence

ORD record
ord-959dd86657c84975ac0ec7fc174a90db
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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