HCID 21090739, compound → HCID 21091048, compound

HRID 351265Notes

Reaction equation

HRID 351265 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH2:22])=[CH:17][CH:16]=3)=[CH:13][C:12]([C:25]([F:28])([F:27])[F:26])=[N:11]2)=[CH:6][CH:5]=1.[O:29]([C:31]#[N:32])[Na]>O.CCO>[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][NH:22][C:31]([NH2:32])=[O:29])=[CH:17][CH:16]=3)=[CH:13][C:12]([C:25]([F:28])([F:26])[F:27])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 21090739HCID 21090739, compoundHCID 178418852HCID 178418852, compound

Product 1

HCID 21091048HCID 21091048, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of (2-{4-[1-[4-(methylthio)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}ethyl)amine hydrochloride (7.5 g) in H2O (150 ml) and EtOH (75 ml) was added NaOCN (2.27 g) at room temperature. pH was adjusted to 6.3 with 1NHCl . The mixture was stirred for 5 hours under the condition of pH 6.0–7.0. The reaction mixture was extracted with EtOAc and washed with dil. NaCl (twice), dried over MgSO4, filtered and evaporated. The residue was column chromatographed on silica gel (CH2Cl2/MeOH) and evaporated. The residue was crytalized from IPE/EtOH. Recrystalized from EtOH/H2O (50 ml–50 ml Final) and dried to give 4.10 g (54%) of N-(2-{4-[1-[4-(methylthio)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}ethyl)urea.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washwashed with dil. NaCl (twice),
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed on silica gel (CH2Cl2/MeOH)
  7. customevaporated
  8. customRecrystalized from EtOH/H2O (50 ml–50 ml Final)
  9. customdried

Sources & evidence

ORD record
ord-c9fdfc2425a346e59e6029fa71f656d0
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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