Sodium Hydroxide → HCID 57637657, compound

HRID 2111479Notes

Reaction equation

HRID 2111479 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[OH-].[Na+].CN(C)[CH2:10][CH2:11][C:12]([C:14]1[O:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[CH:17][CH:18]=1)=O>CO>[NH2:5][C:3]([N:2]1[CH2:10][CH2:11][C:12]([C:14]2[O:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:17][CH:18]=2)=[N:1]1)=[S:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723789ThiosemicarbazideHCID 66952383HCID 66952383, compound

Product 1

HCID 57637657HCID 57637657, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Thiosemicarbazide (1.0 equiv.) was dissolved in MeOH upon heating under nitrogen. Aqueous sodium hydroxide (6 M, 9.0 equiv.) was added to the reaction. A methanol solution of 3-(dimethylamino)-1-[5-(3-chlorophenyl)(2-furyl)]propan-1-one (1.0 equiv) was then added dropwise to the reaction mixture. The solvent was removed and the residue was dissolved in DCM and washed with water, brine, dried over MgSO4, and concentrated. The final compound was purified by preparative-HPLC to give amino{3-[5-(3-chlorophenyl)(2-furyl)](2-pyrazolinyl)}methane-1-thione; LC/MS m/z 306.2 (MH+); Rt=3.06 minutes.

Workup

  1. temperatureupon heating under nitrogen
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe final compound was purified by preparative-HPLC

Sources & evidence

ORD record
ord-e9b840479de64ef292958ca191b4a12e
Source dataset
uspto-grants-2009_04
Patent number
US07521062B2

Reaction notes

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