Water → HCID 12562683, compound

HRID 1606013Notes

Reaction equation

HRID 1606013 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[C:7]=2[CH:18]=1.[C-:19]#[N:20].[Na+].[I-].[Na+].O>CN(C)C=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[C:7]3[CH:18]=[C:3]([CH2:2][C:19]#[N:20])[CH:4]=[CH:5][C:6]=3[O:10][N:9]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 12562677HCID 12562677, compound

Product 1

HCID 12562683HCID 12562683, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromomethyl-3-(4-chlorophenyl)-1,2-benzisoxazole(6.5g.), sodium cyanide (1.1g) and dry sodium iodide (0.3g) were stirred together in dry dimethylformamide (50ml) for 20 hours at ambient temperature. The mixture was poured into water (500ml.), stirred for one hour and the brown solid filtered off, washed and dried (5.1g). This was recrystallised, with charcoaling, from 50% toluene/60-80 petrol ether (100ml.) To give the title compound as an off-white solid (3.4g) m.p. 118°C.

Workup

  1. filtrationthe brown solid filtered off
  2. washwashed
  3. customdried (5.1g)
  4. customThis was recrystallised, with charcoaling, from 50% toluene/60-80 petrol ether (100ml.)

Sources & evidence

ORD record
ord-6d6719119b5e493b9c693fa5b010fb0b
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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