Water → N-(1-phenyl-3-pyrazolidinone-2-ylmethyl)saccharin

HRID 1249137Notes

Reaction equation

HRID 1249137 reaction equation
Br[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:4]1(=[O:6])=[O:5].[C:15]1([N:21]2[CH2:25][CH2:24][C:23](=[O:26])[NH:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>O1CCCC1>[C:15]1([N:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2[CH2:2][N:3]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:4]2(=[O:6])=[O:5])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7090PhenidoneHCID 8471TriethylamineHCID 15225519N-Bromomethylsaccharin

Product 1

HCID 20224974N-(1-phenyl-3-pyrazolidinone-2-ylmethyl)saccharinYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Bromomethylsaccharin (13.8 g), 1-phenyl-3-pyrazolidinone (11.9 g) and triethylamine (5.5 g) were dissolved in tetrahydrofuran (200 ml), and stirred in a stream of nitrogen at room temperature for 2 hours. The reaction mixture was added to water (200 ml), and extracted with 100 ml each of ethyl acetate two times. After drying the extract over anhydrous Glauber's salt, the solvent was distilled away. The thus obtained crude product was recrystallized from ethyl acetate to yield 16 g of N-(1-phenyl-3-pyrazolidinone-2-ylmethyl)saccharin (Compound (I)-(18)). Melting Point: 209°-213° C.

Workup

  1. extractionextracted with 100 ml each of ethyl acetate two times
  2. customAfter drying the
  3. extractionextract over anhydrous Glauber's salt
  4. distillationthe solvent was distilled away
  5. customThe thus obtained crude product
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e33fd103d6a4416f9e7bf1ca6b56b815
Source dataset
uspto-grants-1986_12
Patent number
US04629683

Reaction notes

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