Phenyl Isothiocyanate → HCID 178480600, compound

HRID 2052064Notes

Reaction equation

HRID 2052064 reaction equation
I.[NH2:2][C:3]1[N:4]([CH3:8])[CH2:5][CH2:6][N:7]=1.[OH-].[Na+].[C:11]1([N:17]=[C:18]=[S:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:8][N:4]1[CH2:5][CH2:6][NH:7][C:3]1=[N:2][C:18]([NH:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[S:19]

Participants

4

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 14798Sodium HydroxideHCID 20378480HCID 20378480, compound

Product 1

HCID 178480600HCID 178480600, compoundYield 86.1%

Procedure

2-Amino-1-methylimidazoline hydroiodide (26.75 g, 0.117 mole) is converted to its free base form by treatment with 50% sodium hydroxide. The base is extracted with methylene chloride and the extract dried over potassium carbonate and filtered. To this solution is added phenylisothiocyanate (15.81 g, 0.117 mole) and the reaction mixture is refluxed for three hours. The hot solution is filtered, concentrated to a small volume in vacuo, ether added, chilled, and the solid filtered off to give 23.6 g (86.1%) of N-(1-methyl-2-imidazolidinylidene)-N'-phenylthiourea; m.p. 205°-208° C.

Workup

  1. extractionThe base is extracted with methylene chloride
  2. dry with materialthe extract dried over potassium carbonate
  3. filtrationfiltered
  4. temperaturethe reaction mixture is refluxed for three hours
  5. filtrationThe hot solution is filtered
  6. concentrationconcentrated to a small volume in vacuo, ether
  7. additionadded
  8. temperaturechilled
  9. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-56549edcbc5647fdae9d8372655f01fa
Source dataset
uspto-grants-1980_01
Patent number
US04182865

Reaction notes

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