1,3-Propanediol → HCID 58932585, compound

HRID 853861Notes

Reaction equation

HRID 853861 reaction equation
[CH2:1]([N:8]([CH3:23])[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](O)[CH2:25][CH2:26][OH:27].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([N:8]([CH3:23])[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]12[O:27][CH2:26][CH2:25][CH2:24][O:22]1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 58932539HCID 58932539, compound

Product 1

HCID 58932585HCID 58932585, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-benzyl-N-methyl-2,3-dioxoindoline-5-sulfonamide (2.88 g, 7.8 mmol), 1,3-propane-diol (1.43 mL, 19.5 mmol, 2.5 eq) and para toluene-sulfonic acid hydrate (0.296 g, 1.56 mmol, 0.2 eq) in benzene (135 mL) was refluxed with a Dean Stark Trap for 3.5 hours and stirred at room temperature overnight. The reaction was washed with NaHCO3 (2×), water (2×) and brine (2×) and concentrated. The crude product was purified on Biotage KP silica gel eluting with a step gradient of 35/65 to 45/55 Pet. ether/EtOAc to give the title compound as a bright yellow solid (1.33 g, 44% yield). NMR (300 MHz, DMSO-d6): consistent.

Workup

  1. temperaturewas refluxed with a Dean Stark Trap for 3.5 hours
  2. washThe reaction was washed with NaHCO3 (2×), water (2×) and brine (2×)
  3. concentrationconcentrated
  4. customThe crude product was purified on Biotage KP silica gel eluting with a step gradient of 35/65 to 45/55 Pet. ether/EtOAc

Sources & evidence

ORD record
ord-219a7a7c97c640c8a7d9de0119ea908d
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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