Ammonia → HCID 22165685, compound

HRID 1723076Notes

Reaction equation

HRID 1723076 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH2:10]Br)[C:6]=2[CH:12]=1.CN(C)C([N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1)=O.N>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH2:10][N:19]3[C:20]([CH3:22])=[CH:21][N:17]=[CH:18]3)[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14231157HCID 14231157, compoundHCID 14575000HCID 14575000, compound

Product 1

HCID 22165685HCID 22165685, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution containing 5-chloro-3-bromomethyl-1,2-benzisoxazole (2.5 g, 0.010 mole) and 1-dimethylcarbamoyl-4-methyl-imidazole (1.84 g, 0.012 mole) in anhydrous acetonitrile (25 mL) is stirred at reflux for 72 hours. The solution is cooled to 5° C. (ice-bath) and ammonia gas is bubbled through the solution for 5 minutes after which the solution is allowed to stand at ambient temperature for 1 hour. The solvent is evaporated and the residue is taken up in methylene chloride (25 mL). This solution is washed with water (2×20 mL), dried over anhydrous sodium sulphate, filtered and evaporated to give 5-chloro-3-[(5-methyl-1H-imidazol-1-yl)-methyl]-1,2-benzisoxazole as an oil. A solution of this product in acetone is treated with a slight excess of ethereal hydrogen chloride to afford the hydrochloride salt, m.p. 245°-247° C.

Workup

  1. temperatureat reflux for 72 hours
  2. customis bubbled through the solution for 5 minutes after which the solution
  3. customThe solvent is evaporated
  4. washThis solution is washed with water (2×20 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-917845ee536d457a91a5725c2184369c
Source dataset
uspto-grants-1989_08
Patent number
US04859691

Reaction notes

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