Ethanol → HCID 67440419, compound

HRID 1890263Notes

Reaction equation

HRID 1890263 reaction equation
N[C:2](N)=[S:3].Cl[CH2:6][C:7]1[NH:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1.[CH2:18](O)C>>[C:12]1([C:9]2[CH:8]=[C:7]3[CH2:6][S:3][CH2:2][CH2:18][N:11]3[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 23249595HCID 23249595, compound

Product 1

HCID 67440419HCID 67440419, compound

Conditions

Temperature
20 °C

Procedure

4.42 g (58 mmol) of thiourea are added to a solution of 5.59 g (29 mmol) of 5-(chloromethyl)-3-phenyl-1H-pyrazole in 200 ml of ethanol. The mixture is stirred at 20° C. for 2 days. Most of the solvent is then removed from the mixture, and 10-20 ml of dichloromethane are added. After brief stirring, the precipitate is filtered off with suction and dried. This gives 6.3 g of a product mixture which is used further without further purification. 4.19 g of this mixture are taken up again in 140 ml of N,N-dimethylformamide. 4.55 g of dried potassium carbonate and 4.74 ml of 1,2-dibromoethane are added to this mixture. The mixture is then stirred at 60° C. for 18 h. The reaction mixture is then carefully stirred into water. The aqueous phase is then decanted off, and ethyl acetate is added to the oily residue. The organic phase is dried over Na2SO4 and concentrated. Purification is carried out by silica gel chromatography (cyclohexane/ethyl acetate). This gives 620 mg of the desired product; log P(HCOOH): 2.46; 1H-NMR (ppm): δ (DMSO-d6)=3.20 (t, 2H), 3.94 (s, 2H), 4.32 (t, 2H), 6.54 (s, 1H), 7.31 (t, 1H), 7.40 (t, 2H), 7.65 (d, 2H).

Workup

  1. customMost of the solvent is then removed from the mixture, and 10-20 ml of dichloromethane
  2. additionare added
  3. filtrationAfter brief stirring, the precipitate is filtered off with suction
  4. customdried
  5. customThis gives 6.3 g of a product mixture which is used further without further purification
  6. addition4.55 g of dried potassium carbonate and 4.74 ml of 1,2-dibromoethane are added to this mixture
  7. stirringThe mixture is then stirred at 60° C. for 18 h
  8. stirringThe reaction mixture is then carefully stirred into water
  9. customThe aqueous phase is then decanted off
  10. additionethyl acetate is added to the oily residue
  11. dry with materialThe organic phase is dried over Na2SO4
  12. concentrationconcentrated
  13. customPurification

Sources & evidence

ORD record
ord-c6131c4b6d484d31b293f9ab372c3cb6
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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