Methyl iodide → HCID 69513902, compound

HRID 349416Notes

Reaction equation

HRID 349416 reaction equation
CI.[NH2:3][C:4]1[C:8]([NH:9][C:10]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=S)=[C:7]([CH3:21])[S:6][C:5]=1[CH3:22]>C(O)C>[ClH:19].[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[NH:12][C:10]1[NH:9][C:8]2=[C:7]([CH3:21])[S:6][C:5]([CH3:22])=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86037737N-(3-Amino-2,5-dimethyl-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

Product 1

HCID 69513902HCID 69513902, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.664 g of methyl iodide was added to a solution of 0.27 g of N-(3-amino-2,5-dimethyl-4-thienyl)-N′-(2,6-dichlorophenyl)thiourea in 30 ml of anhydrous ethanol and the mixture was boiled under reflux conditions for approx. 10 hours. After the solvent had been distilled off on a Rotavapor, the residue was admixed with water and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was distilled off on a Rotavapor. The residue was then purified by column chromatography on silica gel using a mixture of 20 parts by volume of ethyl acetate, 10 parts by volume of n-heptane, 3 parts by volume of glacial acetic acid. After the solvent had been distilled off, the residue was dissolved in a little ethyl acetate, made strongly acidic using a hydrogen chloride gas-saturated diethyl ether solution, and the amorphous precipitate was fully crystallized by heating. M.p. 270–273° C.

Workup

  1. distillationAfter the solvent had been distilled off on a Rotavapor
  2. extractionextracted repeatedly with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. distillationthe solvent was distilled off on a Rotavapor
  5. customThe residue was then purified by column chromatography on silica gel using
  6. additiona mixture of 20 parts by volume of ethyl acetate, 10 parts by volume of n-heptane, 3 parts by volume of glacial acetic acid
  7. distillationAfter the solvent had been distilled off
  8. dissolutionthe residue was dissolved in a little ethyl acetate
  9. customthe amorphous precipitate was fully crystallized
  10. temperatureby heating

Sources & evidence

ORD record
ord-1e6c4c0a039340af8a448e9b8876dd86
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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