HCID 15017241, compound → HCID 15017242, compound

HRID 1165716Notes

Reaction equation

HRID 1165716 reaction equation
[CH3:1][C:2]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)=O)([C:6](=[S:8])[NH2:7])[CH:3]([CH3:5])[CH3:4]>C1COCC1.[OH-].[Na+]>[CH:3]([C:2]1([CH3:1])[C:6](=[S:8])[NH:7][C:10]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[N:9]1)([CH3:5])[CH3:4]

Participants

4

Reactant 1

HCID 15017241HCID 15017241, compound

Product 1

HCID 15017242HCID 15017242, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

A solution containing 4.7 g N-[1,2-dimethyl-1-(thiocarbamoyl)propyl]-m-toluamide in 75 mL THF and 35 mL 10% NaOH is heated at 65° C. for 18 hours. The THF is removed in vacuo and the pH of the cooled residue adjusted to 3 with concentrated H2SO4. The product is extracted into CH2Cl2, the extract washed with brine, dried and concentrated to give a yellow solid. This is recrystallized from acetonitrile to give analytically pure 4-isopropyl-4-methyl-2-m-tolyl-2-imidazolin-5-thione, mp 122°-123° C.

Workup

  1. customThe THF is removed in vacuo
  2. extractionThe product is extracted into CH2Cl2
  3. washthe extract washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customThis is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-757991ae5af04a63ad0188c087e431fb
Source dataset
uspto-grants-1990_03
Patent number
US04911747

Reaction notes

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