Methyl malonyl chloride → HCID 67251426, compound

HRID 2420989Notes

Reaction equation

HRID 2420989 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([C:16]([NH:18][NH2:19])=[O:17])=[CH:5][N:4]=1.[C:20](=O)([O-])[OH:21].[Na+].ClC([CH2:28][C:29]([O:31][CH3:32])=[O:30])=O>C(Cl)(Cl)Cl>[C:29]([O:31][CH2:32][C:20]([NH:19][NH:18][C:16]([C:6]1[C:7]([O:9][CH2:10][CH2:11][Si:12]([CH3:14])([CH3:15])[CH3:13])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1)=[O:17])=[O:21])(=[O:30])[CH3:28]

Participants

5

Reactant 3

HCID 123460Methyl malonyl chlorideHCID 516892Sodium BicarbonateHCID 67250367HCID 67250367, compound2×

Product 1

HCID 67251426HCID 67251426, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-Methylthio-4-(2-trimethylsilylethoxy)pyrimidine-5-carbohydrazide [Compound (E) in which R1 represents 2-trimethylsilylethoxy] (1.00 g, 3.33 mmol) obtained in Step 3 of Reference Example 3 was dissolved in chloroform (10 mL), and a saturated aqueous sodium hydrogencarbonate solution (10 mL) was added thereto. While stirring the mixture under ice-cooling, a chloroform (10 mL) solution of methyl chlorocarbonylacetate (0.477 g, 3.50 mmol) was added to the mixture, and was stirred at the same temperature for 1 hour. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was separated into organic layer and aqueous layer. The aqueous layer was extracted with chloroform and the extract was combined with the organic layer. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give crude N′-acetoxymethylcarbonyl-2-methylthio-4-(2-trimethylsilylethoxy)pyrimidine-5-carbohydrazide [Compound (G) in which R1 is 2-trimethylsilylethoxy, and R3B represents acetoxymethyl].

Workup

  1. temperaturecooling
  2. stirringwas stirred at the same temperature for 1 hour
  3. customthe reaction mixture was separated into organic layer and aqueous layer
  4. extractionThe aqueous layer was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-20bb9d6a94314df6885cf7f3ea039d0a
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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