Dimethylformamide → HCID 14012525, compound

HRID 652930Notes

Reaction equation

HRID 652930 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].[CH3:23][N:24](C)[CH:25]=O>>[CH3:23][N:24]([CH3:25])[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

3

Reactant 2

HCID 6228DimethylformamideHCID 20150513HCID 20150513, compound

Product 1

HCID 14012525HCID 14012525, compound

Procedure

A solution of 3.5 g of {[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetyl chloride in 35 ml dimethylformamide is heated at 100° C. for 4 hr. The reaction mixture is then poured into ice, acidified and extracted with ether (4×200 ml). The organic extracts are washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to afford an oil which crystallizes on trituration with ether/petroleum ether. Chromatography on silica gel affords N,N-dimethyl{[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetamide mp 116° C.

Workup

  1. additionThe reaction mixture is then poured into ice
  2. extractionextracted with ether (4×200 ml)
  3. washThe organic extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customto afford an oil which
  8. customcrystallizes on trituration with ether/petroleum ether

Sources & evidence

ORD record
ord-a6c47bb49fdd436f80d68d5b835463ab
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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