Dimethyl Sulfate → HCID 178481547, compound

HRID 1075773Notes

Reaction equation

HRID 1075773 reaction equation
COS([O:6][CH3:7])(=O)=O.[Cl:8][C:9]1[N:15]=[CH:14][C:13]2[NH:16][C:17](=O)[CH2:18][NH:19][C:12]=2[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1.CC(C)([O-])C.[K+]>C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:8][C:9]1[N:15]=[CH:14][C:13]2[N:16]([CH3:17])[C:7](=[O:6])[CH2:18][NH:19][C:12]=2[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 23665647Potassium tert-butoxideHCID 178516730HCID 178516730, compound

Product 1

HCID 178481547HCID 178481547, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

Dimethylsulfate, 1.15g (9mmol), was added to a solution of 1.2g (4.4mmol) of 7-chloro-1,3-dihydro-5-phenyl-2H-pyrazino[2,3-f] [1,4] diazepin-2-one and 1g (9mmol) of potassium t-butoxide in 30 ml of ethanol. After stirring for 10 min at room temperature, the reaction mixture was diluted with 10% aqueous sodium carbonate solution and was extracted with methylene chloride. The extracts were washed with water, dried over sodiumsulfate and evaporated. The residue was chromatographed over 40g of silica gel (Merck, 70-230 mesh) using 10% ethylacetate in methylene chloride. The combined clean fractions were evaporated and the residue was crystallized from ether/hexane to yield the above-named product, with mp. 105°-107°.

Workup

  1. extractionwas extracted with methylene chloride
  2. washThe extracts were washed with water
  3. dry with materialdried over sodiumsulfate
  4. customevaporated
  5. customThe residue was chromatographed over 40g of silica gel (Merck, 70-230 mesh)
  6. customThe combined clean fractions were evaporated
  7. customthe residue was crystallized from ether/hexane
  8. customto yield the above-named product

Sources & evidence

ORD record
ord-95459d84094d4c9ab553ed7e7c5f724f
Source dataset
uspto-grants-1976_05
Patent number
US03954753

Reaction notes

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