Acetone → HCID 178426523, compound

HRID 2057625Notes

Reaction equation

HRID 2057625 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH2:10])=S)=[CH:3][CH:2]=1.CC(C)=O.C[I:17].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>CCOCC>[IH:17].[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([NH:7][C:8]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[NH:10])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 31268PyrrolidineHCID 722833p-Tolylthiourea

Product 1

HCID 178426523HCID 178426523, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Tolylthiourea (33.2 g., 0.2 mole) in 200 ml. acetone is heated under reflux for 3 hrs. with methyliodide (31.4 g., 0.221 mole). Solvent is removed in vacuo and the resulting 2-methyl-1-(4-tolyl)-2-thiopseudourea hydroiodide dissolved in 200 ml. tert-butanol. Pyrrolidine (28.4 g., 0.4 mole) is added and the mixture heated at reflux for 18 hrs. The reaction mixture is cooled, diluted with ether and the resulting solid separated. Recrystallization from acetone-ether affords N-(4-tolyl)-1-pyrrolidinecarboximidamide hydroiodide, m.p. 166°-168° C. Conventional treatment of the salt in CH2Cl2 with aqueous (10-20%) NaOH affords the corresponding free base.

Workup

  1. temperatureunder reflux for 3 hrs
  2. customSolvent is removed in vacuo
  3. dissolutionthe resulting 2-methyl-1-(4-tolyl)-2-thiopseudourea hydroiodide dissolved in 200 ml
  4. temperaturethe mixture heated
  5. temperatureat reflux for 18 hrs
  6. temperatureThe reaction mixture is cooled
  7. customthe resulting solid separated
  8. customRecrystallization from acetone-ether

Sources & evidence

ORD record
ord-994d0c81d6cc48d5a2230df986a0a5a2
Source dataset
uspto-grants-1980_07
Patent number
US04211867

Reaction notes

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