4-Toluenesulfonyl chloride → 2-(2-Trifluoromethylphenylamino)-1H-thieno[3,4-d]imidazole hydrochloride

HRID 349423Notes

Reaction equation

HRID 349423 reaction equation
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.[NH2:12][C:13]1[C:17]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])=S)=[CH:16][S:15][CH:14]=1.[OH-].[Na+]>C1COCC1.O>[ClH:10].[F:29][C:28]([F:31])([F:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19]1[NH:18][C:17]2=[CH:16][S:15][CH:14]=[C:13]2[N:12]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 86037742N-(3-Amino-4-thienyl)-N'-(2-trifluoromethylphenyl)thiourea

Product 1

HCID 695138092-(2-Trifluoromethylphenylamino)-1H-thieno[3,4-d]imidazole hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 165.3 mg of p-toluenesulfonyl chloride in 5 ml of THF was added dropwise to a mixture prepared from a solution of 250 mg of N-(3-amino-4-thienyl)-N′-(2-trifluoromethylphenyl)thiourea in 15 ml of THF and a solution of 77.8 mg of NaOH in 3 ml of water. After stirring at room temperature for 2 hours, the solvent was distilled off, and the residue was admixed with water and extracted with ethyl acetate. After the washing, the organic phase was dried over sodium sulfate, the solvent was distilled off and the residue was 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 and 3 parts by volume of glacial acetic acid. After the solvent of the fraction which had been identified by the LC-MS technique had been distilled off, the residue was dissolved in a little ethyl acetate, made strongly acidic using a solution of hydrogen chloride gas in diethyl ether, and the crystals were filtered off after having been left to stand overnight.

Workup

  1. distillationthe solvent was distilled off
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter the washing, the organic phase was dried over sodium sulfate
  4. distillationthe solvent was distilled off
  5. customthe residue was 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 and 3 parts by volume of glacial acetic acid
  7. distillationhad been distilled off
  8. dissolutionthe residue was dissolved in a little ethyl acetate
  9. filtrationthe crystals were filtered off
  10. waitafter having been left
  11. waitto stand overnight

Sources & evidence

ORD record
ord-edfb351b9ab546dd90a4228ae78c8702
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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