2-Aminothiophenol → HCID 18937681, compound

HRID 2293337Notes

Reaction equation

HRID 2293337 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].Cl[C:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:15]=[N:14][C:13]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O1CCCC1.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:12]1[N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:15]=[N:14][C:13]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 3

HCID 87132-AminothiophenolHCID 24758Sodium hydrideHCID 12937508HCID 12937508, compound

Product 1

HCID 18937681HCID 18937681, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under the argon atmosphere, to an ice-cooled solution of 2-aminobenzenethiol (0.20 ml, 1.87 mmole) in tetrahydrofuran (15 ml) was added 60% sodium hydride (76 mg, 1.90 mmole), and the mixture was stirred at room temperature for 30 minutes. Ethyl 5-chloro-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate (499 mg, 1.69 mmole) was then added, and the mixture was stirred under ice-cooling for 30 minutes and at room temperature for further 3 hours. The reaction mixture was diluted with water, extracted with ethyl acetate, and washed with water and a saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1-1:4) to give ethyl 5-(2-aminophenylthio)-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylate (594 mg, 91.4%).

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 30 minutes and at room temperature for further 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1-1:4)

Sources & evidence

ORD record
ord-8c37e7fbce764f39a2f777fd08acadf1
Source dataset
uspto-grants-1997_11
Patent number
US05686442

Reaction notes

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