Dimethyl Sulfoxide → HCID 178516530, compound

HRID 928245Notes

Reaction equation

HRID 928245 reaction equation
[C:1]1([C:11]2[CH:23]=[C:14]3[NH:15][CH:16]=[C:17](C(O)=O)[C:18](=[O:19])[N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CS(C)=O.[Cl-].[Na+]>O>[C:1]1([C:11]2[CH:23]=[C:14]3[NH:15][CH:16]=[CH:17][C:18](=[O:19])[N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 5234Sodium ChlorideHCID 178524785HCID 178524785, compound

Product 1

HCID 178516530HCID 178516530, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-(1-naphthyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (2.00 g, 6.55 mmol) is stirred in dimethyl sulfoxide (5.06 mL, 71.2 mol) in a 350 mL sealed reaction vessel. Sodium chloride (0.545 g, 9.33 mol) is dissolved in water (2.26 mL) and added to the reaction mixture. The reaction is heated at 150° C. for 3 days during which time an additional 8 mL of DMSO is added along with 15 mL of additional water. The resulting precipitate is collected in a Buchner funnel to provide 2-(naphthalen-1-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (1.48 g, 87%). LCMS: (AA) M+1 262.

Workup

  1. customsealed
  2. customreaction vessel
  3. additionadded to the reaction mixture
  4. customThe resulting precipitate is collected in a Buchner funnel

Sources & evidence

ORD record
ord-ae2b02ce7cda4a388891dbad8f904a31
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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