Tetrahydrofuran → HCID 15338609, compound

HRID 1456364Notes

Reaction equation

HRID 1456364 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(=O)([O-])O.[Na+].[C:12]1([CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:23]3[C:24]([NH2:27])=[N:25][O:26][C:22]=3[CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O1CCCC1>O>[C:12]1([CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:23]3[C:24]([NH:27][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[N:25][O:26][C:22]=3[CH:21]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 15338608HCID 15338608, compound

Product 1

HCID 15338609HCID 15338609, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.8 ml (0.092 mol) of ethyl chloroformate and 10.6 g (0.126 mol) of sodium hydrogen carbonate are added to a solution of 10.1 g (0.042 mol) of 6-(phenylmethoxy)-1,2-benzisoxazol-3-amine in 100 ml of a 9:1 mixture of tetrahydrofuran and water. The mixture is stirred for 18 hours and then the solvent is evaporated off and the residue is treated with dichloromethane and water. The organic phase is decanted off, dried over sodium sulphate and concentrated under reduced pressure. After crystallization from isopropyl alcohol and recrystallization from n-butanol, 11.5 g of product are obtained.

Workup

  1. customthe solvent is evaporated off
  2. additionthe residue is treated with dichloromethane and water
  3. customThe organic phase is decanted off
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customAfter crystallization
  7. customfrom isopropyl alcohol and recrystallization from n-butanol, 11.5 g of product
  8. customare obtained

Sources & evidence

ORD record
ord-c3c6d0a8d5d0404e9df8301ca890ebba
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

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