Chlorosulfonic acid → HCID 178527427, compound

HRID 1484983Notes

Reaction equation

HRID 1484983 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[N:7]=[C:6]([OH:15])[CH:5]=2)[CH2:3][CH2:2]1.[S:16]([Cl:20])(=O)(=[O:18])[OH:17]>>[CH:1]1([C:4]2[CH:5]=[C:6]([OH:15])[N:7]=[C:8]([C:10]3[S:11][C:12]([S:16]([Cl:20])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[N:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178515476HCID 178515476, compound

Product 1

HCID 178527427HCID 178527427, compound

Procedure

6-Cyclopropyl-2-(thiophen-2-yl)pyrimidin-4-ol (2.5 g, 11.46 mmol) in sulfurochloridic acid (30 mL) was stirred at rt for 7 days. The solution was poured into ice-water while stirring vigorously. The mixture was maintained below 25° C. during the quenching, the reaction mixture was extracted with EA (3) and the combined organic layers were washed (cold water), dried (Na2SO4) and concentrated to provide the crude product 5-(4-cyclopropyl-6-hydroxypyrimidin-2-yl)thiophene-2-sulfonyl chloride which is used for the subsequent step without further purification. LC-MS (m/z)=316.1 [M+H]+

Workup

  1. temperatureThe mixture was maintained below 25° C. during the quenching
  2. extractionthe reaction mixture was extracted with EA (3)
  3. washthe combined organic layers were washed (cold water)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f9ed1064e254d169f3d10457b5889fe
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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