Methylamine hydrochloride → HCID 14012523, compound

HRID 652929Notes

Reaction equation

HRID 652929 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.[CH3:24][NH2:25]>C(Cl)Cl.[OH-].[Na+]>[CH3:24][NH:25][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 6364545Methylamine 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 dropwise to a solution of 0.9 g of methylamine 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-ee5ed3694b6d4adc894ba8d70c1d87dd
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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