Hydrochloric Acid → 2-Carbamoyl-7-(3-chloro-2-hydroxypropoxy)benzofuran

HRID 1906433Notes

Reaction equation

HRID 1906433 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH2:14][CH:15]3[O:17][CH2:16]3)=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[NH2:2].[ClH:18]>C(Cl)(Cl)Cl>[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH2:14][CH:15]([OH:17])[CH2:16][Cl:18])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 137294032-Carbamoyl-7-(2,3-epoxypropoxy)benzofuran

Product 1

HCID 137294082-Carbamoyl-7-(3-chloro-2-hydroxypropoxy)benzofuran

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

There was suspended 2.3 g of 2-carbamoyl-7-(2,3-epoxypropoxy)benzofuran obtained in Reference Example 1 in 70 ml of chloroform, and thereto 15 ml of concentrated hydrochloric acid was added. Thereafter, the mixture was vigorously stirred at room temperature for 15 minutes. After the chloroform layer was washed with water and dried with magnesium sulfate, the solvent was distilled away from the reaction mixture under reduced pressure. The resultant residue was purified by silica-gel chromatography (eluent: 2 % ethanol-chloroform) to give the desired compound.

Workup

  1. washAfter the chloroform layer was washed with water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe solvent was distilled away from the reaction mixture under reduced pressure
  4. customThe resultant residue was purified by silica-gel chromatography (eluent: 2 % ethanol-chloroform)

Sources & evidence

ORD record
ord-00a4f93f0c5e423b940f80ea6c6f94fd
Source dataset
uspto-grants-1987_03
Patent number
US04652566

Reaction notes

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