Chloroacetone → HCID 20221464, compound

HRID 1657998Notes

Reaction equation

HRID 1657998 reaction equation
[CH:1]([NH:3][CH:4](P(OCC)(OCC)=O)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:6])=[S:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:32][C:33](=O)[CH3:34]>CC(C)=O>[CH3:32][C:33]1[CH2:34][S:2][CH:1]=[N:3][C:4]=1[C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)=[O:6]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 12866380HCID 12866380, compound

Product 1

HCID 20221464HCID 20221464, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of p-methoxybenzyl α-thioformamidodiethylphosphonoacetate (188 mg., 0.5 mmole), powdered potassium carbonate (1.52 mg., 1.1 mmole) and chloro-2-propanone (44μl., 0.55 mmole) in acetone (2.5 ml.) is stirred at room temperature and under a nitrogen atmosphere. After 22 hours stirring, the mixture is filtered and the salts washed with acetone. The combined filtrate and washings are evaporated in vacuo to a dark residue which is shaken with csrbon tetrachloride (3 × 2 ml.). The combined extracts are washed with water (2 × 2 ml.) and saturated brine (2 ml.), dried over magnesium sulfate and evaporated in vacuo to give p-methoxybenzyl 5-methyl-6H-1,3-thiazine-4-carboxylate (116 mg.) as an orange oil.

Workup

  1. stirringAfter 22 hours stirring
  2. filtrationthe mixture is filtered
  3. washthe salts washed with acetone
  4. customThe combined filtrate and washings are evaporated in vacuo to a dark residue which
  5. stirringis shaken with csrbon tetrachloride (3 × 2 ml.)
  6. washThe combined extracts are washed with water (2 × 2 ml.) and saturated brine (2 ml.)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a3bf10ef369648cca615a24f75773f4a
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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