Chlorosulfonic acid → HCID 90419007, compound

HRID 2202372Notes

Reaction equation

HRID 2202372 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([NH:9][CH3:10])[S:8][C:4]=2[CH:3]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Cl:1][C:2]1[CH:3]=[C:4]2[S:8][C:7]([NH:9][CH3:10])=[N:6][C:5]2=[C:11]([S:14]([Cl:13])(=[O:16])=[O:15])[CH:12]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 107743586-Chloro-N-methyl-1,3-benzothiazol-2-amine

Product 1

HCID 90419007HCID 90419007, compound

Procedure

A solution of 6-chloro-N-methylbenzo[d]thiazol-2-amine (500 mg, 2.53 mmol) in chlorosulfonic acid (5 mL) was stirred at 130° c. overnight. The solution was allowed to cool and slowly added to a large excess of ice. The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chorography (silica gel) eluting with PE/EA=1:1 to get the title compound. 1H NMR (CHLOROFORM-d) δ: 7.95 (d, J=1.9 Hz, 1H), 7.89 (d, J=2.1 Hz, 1H), 6.70 (br. s., 1H), 3.16 (d, J=4.3 Hz, 3H). LC-MS: m/z 297 (M+H)+

Workup

  1. customovernight
  2. temperatureto cool
  3. additionslowly added to a large excess of ice
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chorography (silica gel)
  9. washeluting with PE/EA=1:1

Sources & evidence

ORD record
ord-de1ca1b85c264ecd841fe4a6cada572c
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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