2-Methylbenzoxazole → 2-Methyl-1,3-benzoxazole-6-sulfonyl chloride

HRID 409700

Reaction equation

HRID 409700 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1[O:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1>>[CH3:6][C:7]1[O:8][C:9]2[CH:15]=[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

3

Reactant 2

HCID 72252-MethylbenzoxazoleHCID 24638Chlorosulfonic acid

Product 1

HCID 545939422-Methyl-1,3-benzoxazole-6-sulfonyl chlorideYield 59.9%

Conditions

Temperature
117.5 °C

Procedure

Chlorosulfonic acid (12.5 ml, 187.8 mmol) was cooled in an ice bath and 2-methylbenzoxazole (5.0 g, 37.5 mmol) was carefully added drop wise over a period of 15 min. The combined mixture was heated at 115-120° C. for 16 hours. After cooling, the mixture was added very slowly to ca. 100 ml ice/water mix. The white solid that separated was collected by filtration, washed with water until washings were neutral and dried to yield 5.2 g (59%) of Compound 8, whose structure is given below:

Workup

  1. customof 15 min
  2. temperatureAfter cooling
  3. additionmix
  4. customThe white solid that separated
  5. filtrationwas collected by filtration
  6. washwashed with water until washings
  7. customdried

Sources & evidence

ORD record
ord-19cba7e21bd745dd95faab713c599489
Source dataset
uspto-grants-2014_06
Patent number
US08759526B2

Linked notes

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