2-Aminothiophenol → HCID 22629953, compound

HRID 2306872Notes

Reaction equation

HRID 2306872 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Cl:9][C:10]1[CH:19]=[C:18]([CH2:20]Cl)[C:13]2[O:14][CH2:15][O:16][CH2:17][C:12]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[ClH:9].[Cl:9][C:10]1[CH:19]=[C:18]([CH2:20][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])[C:13]2[O:14][CH2:15][O:16][CH2:17][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 27767806-chloro-8-(chloromethyl)-4H-1,3-benzodioxine

Product 1

HCID 22629953HCID 22629953, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-aminothiophenol (1.25 g, 10 mmol), 6-chloro-8-(chloromethyl)-4H-1,3-benzodioxine (2.17 g, 10 mmol) and potassium carbonate (4.10 g, 30 mmol) were combined in absolute ethanol (100 mL) and stirred 18 h. Dilute with ethyl acetate and wash with saturated sodium bicarbonate solution then brine. The solution was dried over sodium sulfate and the solvent removed in vacuo. The residue was dissolved in methanol and treated with MP BH4− resin (Argonaut 3.16 mmol/g) and potassium carbonate for 48 h. The mixture was filtered and the solvent removed in vacuo. The resulting oil was dissolved in dichloromethane and passed through a 5 g plug of silica gel. The solvent was removed in vacuo and the residue was precipitated from diethyl ether with a solution of hydrogen chloride in dioxane to give the product as an off white powder, 2.52 g (74%). MS (ESI+) for C15H14ClNO2S m/z 308 (M+H)+.

Workup

  1. washwash with saturated sodium bicarbonate solution
  2. dry with materialThe solution was dried over sodium sulfate
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in methanol
  5. additiontreated with MP BH4− resin (Argonaut 3.16 mmol/g) and potassium carbonate for 48 h
  6. filtrationThe mixture was filtered
  7. customthe solvent removed in vacuo
  8. dissolutionThe resulting oil was dissolved in dichloromethane
  9. customThe solvent was removed in vacuo
  10. customthe residue was precipitated from diethyl ether with a solution of hydrogen chloride in dioxane
  11. customto give the product as an off white powder, 2.52 g (74%)

Sources & evidence

ORD record
ord-56dfbcb2a8f545b8b8125273e12863b8
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

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