Acrylonitrile → HCID 58932547, compound

HRID 853862Notes

Reaction equation

HRID 853862 reaction equation
[CH2:1]([N:8]([CH3:27])[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:26][CH2:25][CH2:24][CH2:23][O:22]1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[CH2:29]([N+:36](C)(C)C)[C:30]1C=CC=C[CH:31]=1.C(#N)C=C>CCO>[CH2:1]([N:8]([CH3:27])[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:31][CH2:30][C:29]#[N:36])[C:16](=[O:21])[C:15]12[O:26][CH2:25][CH2:24][CH2:23][O:22]1)(=[O:10])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 58932585HCID 58932585, compound

Product 1

HCID 58932547HCID 58932547, compoundYield 348.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of N-benzyl-N-methyl-2′-oxo-1′,2′-dihydrospiro[1,3-dioxane-2,3′-indole]-5′-sulfonamide (1.00 g, 2.57 mmol) and benzyltrimethylammonium hydroxide (40% aqueous sol'n, 0.112 mL, 0.617 mmol, 0.24 mole % ) in absolute EtOH (20 mL) was heated to 78° C. and acrylonitrile (0.424 mL, 6.44 mmol, 2.5 eq) was added drop-wise. The reaction mixture was heated for 40 minutes longer, cooled to room temperature and filtered. The product was washed with ethanol and dried to give the title compound as a white solid (0.95 g, 84% yield). NMR (300 MHz, DMSO-d6): consistent.

Workup

  1. temperatureThe reaction mixture was heated for 40 minutes longer
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washThe product was washed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-09d48c9fae134f02a631271fe14c8636
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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