(Chlorothio)formyl chloride → 5-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one

HRID 1498970Notes

Reaction equation

HRID 1498970 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.Cl[C:14]([S:16]Cl)=[O:15]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:14](=[O:15])[S:16][N:8]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 19741766HCID 19741766, compound

Product 1

HCID 595495245-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml), 4-chloro-2-methoxybenzamide (5.67 g, 30.5 mmol) prepared in the Step 7-1-1 and chlorocarbonylsulfenyl chloride (4.40 g, 33.6 mmol) were suspended, and the mixture was heated under reflux for 1.5 hours. After being allowed to cool, the mixture was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to give the title compound (5.33 g, 71%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-bbbecceb172e405d9d3af1c5778f1aaa
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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