Sulfuryl chloride → Rac-4,6-dichloro-7-methoxy-indan-1-ylamine

HRID 1928762Notes

Reaction equation

HRID 1928762 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[CH:11]([NH2:13])[CH2:10][CH2:9]2.S(Cl)([Cl:17])(=O)=O>C(O)(=O)C>[Cl:1][C:7]1[CH:6]=[C:5]([Cl:17])[C:4]([O:3][CH3:2])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH:11]2[NH2:13]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 667603987-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

Product 1

HCID 68632840Rac-4,6-dichloro-7-methoxy-indan-1-ylamineYield 78,334%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Rac-7-methoxy-indan-1-ylamine hydrochloride (2.20 g, 0.011 mmol) was dissolved in acetic acid (100 mL). After cooling to 0° C. sulfuryl chloride (1.88 mL, 0.23 mmol) was slowly added and the reaction mixture was stirred for 16 h at ambient temperature. Then the solvent was evaporated and the residue was taken up in isopropanol. Thereby a precipitate formed which was isolated and dried on high vacuum to yield rac-4,6-dichloro-7-methoxy-indan-1-ylamine (2.0 g, 68%) as a white solid; MS: m/e=269.6 (M+H+).

Workup

  1. additionwas slowly added
  2. customThen the solvent was evaporated
  3. customThereby a precipitate formed which
  4. customwas isolated
  5. customdried on high vacuum

Sources & evidence

ORD record
ord-f6d9ac20a43b4c1bb6a87d248703daf9
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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