Hydrochloric Acid → HCID 23368568, compound

HRID 1901632Notes

Reaction equation

HRID 1901632 reaction equation
C(OC([NH:8][CH:9]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.ClS([N:33]=[C:34]=[O:35])(=O)=O.O.Cl>C(Cl)Cl.CO.C(Cl)(Cl)Cl.CC(O)C>[ClH:21].[NH2:8][CH:9]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:34](=[O:35])[NH2:33])[CH:23]=1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23368474HCID 23368474, compound

Product 1

HCID 23368568HCID 23368568, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.40 g of 3-[2-tert-butoxycarbonylamino-2-(3-hydroxyphenyl)ethoxy]-5-chloro-1,2-benzoisoxazole in 10 ml of methylene chloride is added 0.20 g of chlorosulfonyl isocyanate at -30° C., and thereafter, the temperature is gradually elevated to 0° C., after which 5 ml of water is added and they are subjected to reaction at the same temperature for 30 minutes. The solvent is removed by distillation under reduced pressure, water and ethyl acetate are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The oily product obtained is dissolved in 20 ml of methanol and 20 ml of chloroform, and 3.0 ml of a 2-propanol solution (6.5M) of hydrogen chloride is added at room temperature. They are subjected to reaction at the same temperature for 18 hours, after which the solvent is removed by distillation under reduced pressure. 2-Propanol is added to the residue obtained, and after stirring, the crystals precipitated are collected by filtration to obtain 0.3 g of colorless, crystalline 3-[2-amino-2-(3-carbamoyloxyphenyl)ethoxy]-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 232.0°-233.5° C.

Workup

  1. customis gradually elevated to 0° C.
  2. customthey are subjected to reaction at the same temperature for 30 minutes
  3. customThe solvent is removed by distillation under reduced pressure, water and ethyl acetate
  4. additionare added to the residue
  5. customobtained
  6. customthe organic layer is separated
  7. washThe separated organic layer is washed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent is removed by distillation under reduced pressure
  10. customThe oily product obtained
  11. customThey are subjected to reaction at the same temperature for 18 hours
  12. customafter which the solvent is removed by distillation under reduced pressure
  13. addition2-Propanol is added to the residue
  14. customobtained
  15. stirringafter stirring
  16. customthe crystals precipitated
  17. filtrationare collected by filtration

Sources & evidence

ORD record
ord-081a4b6c719d41d1b349fa68e47cd3d9
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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