Potassium Carbonate → HCID 20357827, compound

HRID 1658017Notes

Reaction equation

HRID 1658017 reaction equation
[CH:1]([NH:3][CH:4](P(OCCCC)(OCCCC)=O)[C:5]([O:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:10])=[O:6])=[S:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:37][C:38](=O)[CH2:39][O:40][C:41](=[O:45])[CH:42]([CH3:44])[CH3:43]>CC(C)=O>[C:41]([O:40][CH2:39][C:38]1[CH2:37][S:2][CH:1]=[N:3][C:4]=1[C:5]([O:7][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=1)=[O:10])=[O:6])(=[O:45])[CH:42]([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20357895HCID 20357895, compoundHCID 86733536HCID 86733536, compound

Product 1

HCID 20357827HCID 20357827, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of p-bromophenacyl α-thioformamido-dibutylphosphonoacetate (6.10 g) in acetone (50 ml) is treated with powdered potassium carbonate (4.98 g). The mixture is stirred under a nitrogen atmosphere while 1-chloro-3-isobutyryloxy-2-propanone (2.32 g) in acetone (10 ml) is added dropwise over 10 minutes. The reaction mixture is stirred an additional 3 hours at room temperature, then filtered. Evaporaton of the filtrate under reduced pressure leaves a dark oil which is extracted with carbon tetrachloride (2 × 50 ml). The combined extracts are washed with 0.5 M dipotassium hydrogen phosphate, water, and saturated brine, dried over magnesium sulfate, and evaporaged in vacuo to give crude p-bromophenacyl 5-isobutyryloxymethyl-6H-1,3-thiazine-4-carboxylate.

Workup

  1. additionis added dropwise over 10 minutes
  2. filtrationfiltered
  3. customEvaporaton of the filtrate under reduced pressure leaves a dark oil which
  4. extractionis extracted with carbon tetrachloride (2 × 50 ml)
  5. washThe combined extracts are washed with 0.5 M dipotassium hydrogen phosphate, water, and saturated brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-2537bd267e9240ba83c07a666fba4392
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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