Water → HCID 14835371, compound

HRID 1199001Notes

Reaction equation

HRID 1199001 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[C:14]2[C:10](=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[O:12][N:13]=2)[CH:9]=[CH:8][CH:7]=1.O>CS(C)=O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:11]1[O:12][N:13]=[C:14]2[C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=[CH:9][C:10]=12

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 14835370HCID 14835370, compound

Product 1

HCID 14835371HCID 14835371, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a slurry of 1.8 g (0.028 mole) of potassium cyanide in 80 ml of dimethylsulfoxide at 60° C. was added 9.7 g (0.027 mole) of 7-(bromomethyl)-3-(2,4-dichlorophenyl)-2,1-benzisoxazole. The mixture was heated at 50°-60° C. for 3 hr, poured into 1 liter of water and let stand overnight. The resulting solid was collected by filtration, washed with water and dried to give 7.6 g of crude tan solid. The solid was chromatographed on 160 g of silica gel to give 2.7 g of solid. The solid was recrystallized from carbon tetrachloride (charcoal) and then from acetonitrile to yield 0.7 g (8%) of crystals, m.p. 147°-148° C.

Workup

  1. temperatureThe mixture was heated at 50°-60° C. for 3 hr
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customto give 7.6 g of crude tan solid
  6. customThe solid was chromatographed on 160 g of silica gel

Sources & evidence

ORD record
ord-9c22631d98af4c4d8b977e30d8f7bae5
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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