Chlorosulfonic acid → 4-oxo-1H-quinazoline-8-sulfonyl chloride

HRID 514838Notes

Reaction equation

HRID 514838 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[N:8][CH:7]=1>>[OH:16][C:9]1[C:10]2[C:15](=[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:13]=[CH:12][CH:11]=2)[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178517962HCID 178517962, compound

Product 1

HCID 1785274264-oxo-1H-quinazoline-8-sulfonyl chlorideYield 581.7%

Conditions

Temperature
140 °C

Procedure

Chlorosulfonic acid (4.10 mL, 62.6 mmol) was slowly added to quinazolin-4-ol (1.09 g, 0.26 mmol). The resulting mixture was heated to 140° C. and stirred for 3 hours at the same temperature. After cooling to room temperature, the reaction mixture was poured into crushed ice. The mixture was extracted with DCM (100 mL×3), the combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified via flash chromatography (5% PE:Ethyl Acetate) to give 370 mg of 4-hydroxyquinazoline-8-sulfonyl chloride. 1H NMR (400 MHz, DMSO-d6) δ: 7.76 (t, J=7.79 Hz, 1 H) 8.26 (ddd, J=9.67, 7.92, 1.48 Hz, 2 H) 9.02 (s, 1 H). LC-MS: m/z 245.7 (M+H)+

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured
  3. custominto crushed ice
  4. extractionThe mixture was extracted with DCM (100 mL×3)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified via flash chromatography (5% PE:Ethyl Acetate)

Sources & evidence

ORD record
ord-b65f26ffc55d49589e9f6c5cec26bb54
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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