Acetone → 2-(2,6-Dichlorophenylamino)-1H-thieno[3,4-d]imidazole hydrochloride

HRID 349414Notes

Reaction equation

HRID 349414 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)=[CH:7][S:6][CH:5]=1.Cl.CC(C)=O>C(O)C.C(OCC)(=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=[CH:7][S:6][CH:5]=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 86037735N-(3-Amino-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

Product 1

HCID 695134122-(2,6-Dichlorophenylamino)-1H-thieno[3,4-d]imidazole hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g of methyl iodide were added to a suspension of 0.951 g of N-(3-amino-4-thienyl)-N′-(2,6-dichlorophenyl)thiourea in 40 ml of anhydrous ethanol and the mixture was boiled on a reflux condenser for 6 hours. After the solvent had been distilled off on a Rotavapor, the residue was admixed with water, made alkaline using an aqueous saturated sodium hydrogencarbonate solution and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulfate and treated with activated carbon, and the solvent was distilled off on a Rotavapor. The residue was then purified by column chromatography on silica gel using a mixture of 10 parts by volume of dichloromethane and 1 part by volume of methanol. After the solvent had been distilled off, a brown oily-amorphous product was obtained. It was dissolved in a little ethyl acetate, made strongly acidic using a hydrogen chloride gas-saturated ether solution, and, after adding a little acetone, boiled until complete crystallization. M.p. >300° 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. additiontreated with activated carbon
  5. distillationthe solvent was distilled off on a Rotavapor
  6. customThe residue was then purified by column chromatography on silica gel using
  7. additiona mixture of 10 parts by volume of dichloromethane and 1 part by volume of methanol
  8. distillationAfter the solvent had been distilled off
  9. customa brown oily-amorphous product was obtained
  10. customboiled until complete crystallization

Sources & evidence

ORD record
ord-5aa0891a03c64f6fbe1beb40890b617d
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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