Urea → HCID 118208568, compound

HRID 595222Notes

Reaction equation

HRID 595222 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH:8]([CH2:12][C:13]([OH:15])=O)[C:9](O)=[O:10])[CH:6]=1.[NH2:16]C(N)=O>O>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH:8]2[CH2:12][C:13](=[O:15])[NH:16][C:9]2=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 118208557HCID 118208557, compound

Product 1

HCID 118208568HCID 118208568, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of 2-((4-iodo-1H-pyrazol-1-yl)methyl)succinic acid (170 mg, 0.52 mmol) and urea (72 mg, 1.50 mmol) was stirred neat at 130° C. for 12 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-((4-iodo-1H-pyrazol-1-yl)methyl)pyrrolidine-2,5-dione. MS ESI calc'd. for C8H9IN3O2 [M+H]+ 306. found 306. 1H NMR (400 MHz, CD3OD) δ 7.70 (s, 1H), 7.50 (s, 1H), 4.62-4.43 (m, 2H), 3.48-3.37 (m, 1H), 2.85-2.68 (m, 1H), 2.61-2.49 (m, 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f032db9b4304427ab08be76950746d6d
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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