Ethanol → HCID 59323904, compound

HRID 1715179Notes

Reaction equation

HRID 1715179 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](=O)[CH3:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:16][C:17]([NH2:19])=[S:18].II.CCO>N1C=CC=CC=1.CCOC(C)=O>[CH3:14][C:13]1[N:16]=[C:17]([NH2:19])[S:18][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 807IodineHCID 2723790ThioureaHCID 59323905HCID 59323905, compound

Product 1

HCID 59323904HCID 59323904, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-(4-pyrazol-1-yl-phenyl)-propan-2-one (6.9 g, 34.46 mmol) in pyridine (30 ml) is treated with thiourea (2.6 g, 34.46 mmol) followed by iodine (8.7 g, 34.46 mmol) and heated to 80° C. After 8 hours, the reaction mixture is allowed to cool to room temperature and the resulting suspension is filtered and washed with EtOAc. The filtrate is concentrated in vacuo to afford an oil. The oil is dissolved in EtOAc (200 ml) and washed with NaHCO3 (2×100 ml), brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford a sticky solid. EtOH is added to the crude residue and the resulting precipitate is filtered and dried to afford the title compound (MH+ 257.29).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting suspension is filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto afford an oil
  6. washwashed with NaHCO3 (2×100 ml), brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto afford a sticky solid
  10. filtrationthe resulting precipitate is filtered
  11. customdried

Sources & evidence

ORD record
ord-b982f91176cb4129ab3a0e047ad57e80
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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