Ethyl Acetate → 2-Amino-6-chlorobenzenethiol hydrogen chloride, 95%

HRID 1819780Notes

Reaction equation

HRID 1819780 reaction equation
C([S:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:16])C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-].CCOC(C)=O>C1C=CC=CC=1>[ClH:15].[NH2:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[SH:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 13782476HCID 13782476, compound

Product 1

HCID 185116192-Amino-6-chlorobenzenethiol hydrogen chloride, 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-benzylsulfanyl-3-chloro-phenylamine (204) in 140 mL of benzene at 0° C. was added AlCl3 (Aldrich, 23.8 g, 179 mmol) in portion. The mixture turned to purple. After stirred at ambient temperature overnight, the mixture was poured to ice and EtOAc and stirred for 20 min. The mixture was extracted 3× with EtOAc (500 mL). The organic layers were washed twice with a brine solution (400 mL), dried over Na2SO4, and concentrated under vacuum. The crude product was treated with 145 mL of 1N HCl in ether. The product (13.6 g) was collected by filtration and washed with hexanes. 1H NMR (400 MHz, DMSO) δ 7.05 (t, J=8.2 Hz, 1H), 6.70 (d, J=8.2 Hz, 1H), 6.61 (d, J=7.8 Hz, 1H).

Workup

  1. stirringstirred for 20 min
  2. extractionThe mixture was extracted 3× with EtOAc (500 mL)
  3. washThe organic layers were washed twice with a brine solution (400 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. additionThe crude product was treated with 145 mL of 1N HCl in ether
  7. filtrationThe product (13.6 g) was collected by filtration
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-52b54ae758a746199a7c95c2162f9201
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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