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

HRID 453089Notes

Reaction equation

HRID 453089 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.Cl[C:13]([S:15]Cl)=[O:14]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][C:13](=[O:14])[S:15][N:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 769594-Methoxybenzamide

Product 1

HCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-methoxybenzamide (0.30 g, 1.10 mmol) in toluene (10 ml) was added chlorocarbonylsulfenyl chloride (0.80 ml, 9.92 mmol). The resulting reaction mixture was refluxed at 80° C. for 3 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added diethyl ether and washed with twice with water, twice with 5% NaHCO3, again with water, and was dried (Na2SO4), concentrated under vacuum to give the product (crude yield 0.475 g) that was carried forward to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. concentrationthe mixture was concentrated
  4. additionadded diethyl ether
  5. washwashed with twice with water
  6. dry with materialtwice with 5% NaHCO3, again with water, and was dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto give the product (crude yield 0.475 g) that
  9. customwas carried forward to the next step without further purification

Sources & evidence

ORD record
ord-848742b7949449a7b4dacf7d6e2bf053
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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