Water → HCID 67521263, compound

HRID 1924418Notes

Reaction equation

HRID 1924418 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4](=S)[NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O)[CH3:2].IC.O.[NH2:22][NH2:23].O>CO>[NH2:22][N:23]1[C:8](=[O:10])[C:7]2[C:6](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[C:4]1[N:3]([CH2:1][CH3:2])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24654Hydrazine hydrate (1:1)HCID 44221300HCID 44221300, compound

Product 1

HCID 67521263HCID 67521263, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-(3,3-diethyl-thioureido)benzoate (2.29 g, 8.59 mmol) was dissolved in methanol (15 mL), followed by addition of iodomethane (1.07 mL, 17.2 mmol). The reaction mixture was heated at 80° C. for 10 minutes under microwave conditions making sure the temperature did not exceed 80° C. The reaction mixture was evaporated to dryness and then redissolved in methanol (50 mL). Hydrazine monohydrate (1.25 mL, 25.8 mmol) was added followed by stirring at RT overnight. The reaction mixture was poured into water (200 mL), followed by extraction with diethyl ether (2×100 mL), drying (MgSO4) and evaporation in vacuo. The crude product was subjected to column chromatography (EtOAc/Heptane) giving the title compound (1.37 g, 69%).

Workup

  1. customdid not exceed 80° C
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionredissolved in methanol (50 mL)
  4. extractionfollowed by extraction with diethyl ether (2×100 mL)
  5. customdrying
  6. custom(MgSO4) and evaporation in vacuo

Sources & evidence

ORD record
ord-7a5805840ba344caa6e895d63517086f
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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