Acetic Acid → Isohexane ethyl acetate

HRID 2377017Notes

Reaction equation

HRID 2377017 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[O-:27][C:28]#[N:29].[K+].[C:31]([OH:34])(=[O:33])[CH3:32]>O>[C:31]([O:34][CH2:24][CH3:25])(=[O:33])[CH3:32].[CH3:3][CH2:4][CH2:5][CH:6]([CH3:9])[CH3:7].[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:14]([S:17]([C:20]3[CH:21]=[C:22]([NH:26][C:28]([NH2:29])=[O:27])[CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 21099488HCID 21099488, compound

Product 2

HCID 21099528HCID 21099528, compoundHCID 21882781Isohexane ethyl acetateYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]amine hydrochloride (Example 212, 100 mg, 0.26 mmol) and potassium cyanate (63 mg, 0.78 mol) in acetic acid (3 mL) and water (0.5 mL) was stirred at room temperature for 16 hours. The acetic acid was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium hydrogencarbonate solution and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% ethyl acetate/isohexane then 40% ethyl acetate/isohexane, to give the title compound. δH (500 MHz, d6 DMSO): 8.96 (1H, s), 8.13 (1H, s), 7.86 (2H, d, J=8.5 Hz), 7.79 (2H, d, J=8.5 Hz), 7.67 (2H, dd, J=5.6, 8.7 Hz), 7.54-7.52 (1H, m), 7.44-7.40 (3H, m), 7.27 (1H, d, J=16.4 Hz), 7.22 (2H, t, J=8.8 Hz), 5.98 (2H, s).

Workup

  1. customThe acetic acid was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-b91a54692a664e17bfb1c392a52c5aaa
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

Loading…