Chlorosulfonic acid → HCID 58169543, compound

HRID 1484892Notes

Reaction equation

HRID 1484892 reaction equation
[Cl:1][C:2]1[C:3]([S:13][CH3:14])=[N:4][C:5]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[N:6][CH:7]=1.[Cl:15][S:16](O)(=[O:18])=[O:17]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([S:13][CH3:14])=[N:4][C:5]([C:8]2[O:9][C:10]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:11][CH:12]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 58169399HCID 58169399, compound

Product 1

HCID 58169543HCID 58169543, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-chloro-2-(furan-2-yl)-4-(methylthio)pyrimidine (800 mg, 3.53 mmol, 1.0 equiv.) in CH2Cl2 (5 mL) was added ClSO3H (25 mL) dropwise at −20° C. The reaction mixture was stirred at 25° C. for 2 h, then, quenched with cracked ice at −20° C. The mixture was extracted with ethylacetate. The combined organic layers was dried with Na2SO4 to give a solution of 5-(5-chloro-4-(methylthio)pyrimidin-2-yl)furan-2-sulfonyl chloride in ethylacetate, to which t-butylamine (10 mL) was added. The mixture was stirred at 20° C. for 2 h, then, concentrated. The residue was purified by column chromatography to afford N-tert-butyl-5-(5-chloro-4-(methylthio)pyrimidin-2-yl)furan-2-sulfonamide (147 mg, 12% over 2 steps). LC-MS (m/z)=362.0 [M+H]+.

Workup

  1. customquenched with cracked ice at −20° C
  2. extractionThe mixture was extracted with ethylacetate
  3. dry with materialThe combined organic layers was dried with Na2SO4

Sources & evidence

ORD record
ord-2d5e39d71d634f44baeab00a34b4d7ec
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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