Methyl iodide → HCID 21285451, compound

HRID 2231631Notes

Reaction equation

HRID 2231631 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[C:20]1([N:26]=[C:27]=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:29]I>C1COCC1.CS(C)=O>[CH3:14][C:12]1[CH:11]=[C:10]([CH3:15])[N:9]=[C:8]([N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:27](=[N:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:28][CH3:29])[N:13]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7673Phenyl IsothiocyanateHCID 24758Sodium hydrideHCID 91650PyrimethanilHCID 178418361HCID 178418361, compound

Product 1

HCID 21285451HCID 21285451, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-Anilino-4,6-dimethylpyrimidine (10 g) was added to a suspension of sodium hydride in oil (1.65 g of an 80% suspension) in dry THF (100 ml) and the mixture was heated under reflux until evolution of hydrogen ceased. Phenyl isothiocyanate (6.6 ml) was added slowly to the clear solution. The mixture was then stirred at room temperature for 2 hours. The solid was collected, washed with ether and dried in vacuo to give crude N-(4,6-dimethylpyrimidin-2-yl)-N,N'-diphenylisothiourea sodium salt. To a stirred solution of this product (7.2 g) in dimethyl sulphoxide (10 ml) was added a solution of methyl iodide (1.3 ml) in dimethyl sulphoxide (10 ml). The mixture was stirred at room temperature for 3 hours and then concentrated. The residue was treated with water and then extracted with dichloromethane. The extract was worked up in conventional manner to give N-(4,6-dimethylpyrimidin-2-yl)-S-methyl-N,N'-diphenylisothiourea, m.p. 101°-3°. (Compound 7).

Workup

  1. temperaturethe mixture was heated
  2. customThe solid was collected
  3. washwashed with ether
  4. customdried in vacuo
  5. customto give crude N-(4,6-dimethylpyrimidin-2-yl)-N,N'-diphenylisothiourea sodium salt
  6. stirringThe mixture was stirred at room temperature for 3 hours
  7. concentrationconcentrated
  8. additionThe residue was treated with water
  9. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-e5300408fd774a88874aac36452f6417
Source dataset
uspto-grants-1988_11
Patent number
US04783459

Reaction notes

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