Chlorosulfonic acid → 3-Methyl-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride

HRID 641908Notes

Reaction equation

HRID 641908 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:11].[S:12]([Cl:16])(=O)(=[O:14])[OH:13]>>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([S:12]([Cl:16])(=[O:14])=[O:13])=[CH:10][C:5]=2[O:4][C:3]1=[O:11]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 308462-Benzoxazolinone, 3-methyl-

Product 1

HCID 27720603-Methyl-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chlorideYield 48.5%

Procedure

3-methylbenzo[d]oxazol-2(3H)-one (620 mg, 4.16 mmol) was added, in several batches, to chilled sulfurochloridic acid (17.5 g, 150.86 mmol) at 0° C. The resulting solution was stirred at room temperature for 3 hours, then quenched by adding it slowly to 200 mL of ice/salt. The resulting solution was extracted with ethyl acetate (3×40 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to afford 0.5 g (46%) of 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.97 (s, 1H), 7.16 (d, 1H), 3.52 (s, 3H).

Workup

  1. customquenched
  2. additionby adding it slowly to 200 mL of ice/salt
  3. extractionThe resulting solution was extracted with ethyl acetate (3×40 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ba75b6e00ab42929633f6b5135bbf0e
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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