Potassium Carbonate → HCID 20357801, compound

HRID 1658008Notes

Reaction equation

HRID 1658008 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+].[C:31]([O:34][CH2:35][C:36](=O)[CH2:37]Cl)(=[O:33])[CH3:32]>CC(C)=O>[C:31]([O:34][CH2:35][C:36]1[CH2:37][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])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 12866380HCID 12866380, compound

Product 1

HCID 20357801HCID 20357801, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirring solution of p-methoxybenzyl α-thioformamido-diethylphosphonoacetate (114 mg., 0.3 mmole) in acetone (1.5 ml.) is added powdered potassium carbonate (124 mg., 0.9 mmole). The resulting mixture is stirred for 5 minutes at room temperature and under a nitrogen atmosphere, then treated with a solution of 1-acetoxy-3-chloro-2-propanone (48 mg., 0.32 mmole) in acetone (0.5 ml.). After having been stirred for 3 hours at room temperature, the mixture is filtered to remove the salts which are washed with acetone. The combined filtrate and washings are evaporated in vacuo to a dark oil. The residue is dissolved in carbon tetrachloride (6 ml.), washed with aqueous phosphate (1 ml. of 1M dipotassium phosphate + 2 ml. water) and water (2 × 3 ml.), dried over magnesium sulfate, and evaporated in vacuo to give crude p-methoxybenzyl 5-acetoxymethyl-6H-1,3-thiazine-4-carboxylate (106 mg.) as an organic oil.

Workup

  1. stirringAfter having been stirred for 3 hours at room temperature
  2. filtrationthe mixture is filtered
  3. customto remove the salts which
  4. washare washed with acetone
  5. customThe combined filtrate and washings are evaporated in vacuo to a dark oil
  6. dissolutionThe residue is dissolved in carbon tetrachloride (6 ml.)
  7. washwashed with aqueous phosphate (1 ml. of 1M dipotassium phosphate + 2 ml. water) and water (2 × 3 ml.)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-b447626544dc43a383509636bcdb964f
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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