Ethylamine hydrochloride → HCID 14012523, compound

HRID 568700Notes

Reaction equation

HRID 568700 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][C:20](Cl)=[O:21].Cl.[CH2:24]([NH2:26])C>C(Cl)Cl.[OH-].[Na+]>[CH3:24][NH:26][C:20](=[O:21])[CH2:19][O:18][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])=[N:8][O:9][C:10]=2[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 11198Ethylamine hydrochlorideHCID 20150513HCID 20150513, compound

Product 1

HCID 14012523HCID 14012523, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4.0 g of {[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetyl chloride in methylene chloride is added drop-wise to a solution of 0.9 g of ethylamine hydrochloride in 50 ml methylene chloride and 25 ml of 15% sodium hydroxide solution at 0° C. After 18 hr at room temperature the reaction mixture is acidified, filtered, and the filtrate partitioned. The aqueous solution is washed with methylene chloride. The organic solutions are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solution gives N-methyl-{[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetamide, mp 164° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate partitioned
  3. washThe aqueous solution is washed with methylene chloride
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solution

Sources & evidence

ORD record
ord-2826966806884f76a28a002908b3dbb9
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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