(Chlorothio)formyl chloride → 5-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

HRID 453104Notes

Reaction equation

HRID 453104 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]([S:21]Cl)=[O:20]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:19](=[O:20])[S:21][N:15]=2)=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 27264314-Benzyloxybenzamide

Product 1

HCID 595495255-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-benzyloxybenzamide (0.25 g, 1.10 mmol) in toluene (15 ml) was added chlorocarbonylsulfenyl chloride (0.18 ml, 2.20 mmol) and the resulting reaction mixture was refluxed at 90° C. overnight. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added diethyl ether and washed twice with water, twice with 5% NaHCO3, again with water, and was then dried (Na2SO4), concentrated under vacuum to give the product (crude yield 0.310 g, 98%) that was used as such for the next step.

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 twice with water, twice with 5% NaHCO3, again with water
  6. dry with materialwas then dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto give the product (crude yield 0.310 g, 98%) that

Sources & evidence

ORD record
ord-c25d00487cf4471eb6576890df02807b
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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