Hydrochloric Acid → 3-(2-Amino-3-methylthiocarbamoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride

HRID 1901656Notes

Reaction equation

HRID 1901656 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:19]C(OC(C)(C)C)=O)[CH2:13][O:14][C:15](=[S:18])[NH:16][CH3:17])[C:6]=2[CH:27]=1.O1CCOCC1.Cl.CC(O)C>CO>[ClH:1].[NH2:19][CH:12]([CH2:13][O:14][C:15](=[S:18])[NH:16][CH3:17])[CH2:11][O:10][C:7]1[C:6]2[CH:27]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:9][N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 312751,4-DioxaneHCID 86750033HCID 86750033, compound

Product 1

HCID 233685613-(2-Amino-3-methylthiocarbamoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.4 g of 5-chloro-3-(2-tert-butoxycarbonylamino-3-methylthiocarbamoyloxypropoxy)-1,2-benzoisoxazole in 10 ml of methanol is added 5 ml of a dioxane solution (3.2N) of hydrogen chloride at room temperature, and they are subjected to reaction at the same temperature for three hours, after which the solvent is removed by distillation under reduced pressure. To the residue obtained is added 3 ml of 2-propanol, and the crystals precipitated are collected by filtration, to obtain 0.22 g of pale yellow, crystalline 3-(2-amino-3-methylthiocarbamoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 198.8°-199.2° C. (decomp.).

Workup

  1. customthey are subjected to reaction at the same temperature for three hours
  2. customafter which the solvent is removed by distillation under reduced pressure
  3. customTo the residue obtained
  4. customthe crystals precipitated
  5. filtrationare collected by filtration

Sources & evidence

ORD record
ord-f79c01ee8c7d48ef8f1fc8bdf01e255d
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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