Ethanol → HCID 58528803, compound

HRID 1431018Notes

Reaction equation

HRID 1431018 reaction equation
[I:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[C:13]([S:15][C:16]3[N:17]([CH3:21])[CH:18]=[CH:19][N:20]=3)[CH:14]=2)[C:10]#N)=[CH:4][CH:3]=1.C(O)C.[OH-:27].[Na+].[OH2:29]>>[I:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[C:13]([S:15][C:16]3[N:17]([CH3:21])[CH:18]=[CH:19][N:20]=3)[CH:14]=2)[C:10]([OH:29])=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962Water2×HCID 14798Sodium HydroxideHCID 58528867HCID 58528867, compound

Product 1

HCID 58528803HCID 58528803, compoundYield 90%

Procedure

A mixture of 3-(4-iodo-phenoxy)-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzonitrile (1.60 g, 3.69 mmol), 12 mL, of ethanol, 1.2 mL of water and 1 mL of 50% w/w NaOH in water (18.45 mmol) was microwave heated at 130° C. for 5 min and then cooled to rt. The mixture was concentrated by evaporation and diluted with 20 mL of water, then with stirring, 20 mL of 1 M aqueous NaHSO4 was added. The resulting solid was collected by filtration and dried at 0.1 mm/23° C. for 16 h to provide 1.5 g (90%) of the title compound as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 3.63 (s, 3H), 6.91 (d, 2H, J=8 Hz), 6.94 (t, 1H, J=2 Hz), 7.14 (d, 1H, J=1 Hz), 7.21 (dd, 1H, J=2, 1 Hz), 7.28 (dd, 1H, J=2, 1 Hz), 7.51 (d, 1H, J=1 Hz), 7.75 (d, 2H, J=8 Hz); LCMS (m/z): 453.5 [C17H13IN2O3S+H]+.

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. additiondiluted with 20 mL of water
  3. addition20 mL of 1 M aqueous NaHSO4 was added
  4. filtrationThe resulting solid was collected by filtration
  5. customdried at 0.1 mm/23° C. for 16 h

Sources & evidence

ORD record
ord-5095184937984ace930b92c0e57101e5
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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