18-Crown-6 → HCID 22119936, compound

HRID 1274610Notes

Reaction equation

HRID 1274610 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[N-:25]=[N+:26]=[N-:27].[Na+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[N:25]([CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1)=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 33557Sodium AzideHCID 22119928HCID 22119928, compound

Product 1

HCID 22119936HCID 22119936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (2.00 g, 4.76 mmol) in N,N-dimethylformamide is treated with sodium azide (0.325 g, 5.00 mmol), stirred overnight at room temperature, treated with 18-crown-6, stirred at room temperature for two hours, and poured into an ice-water mixture. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and air-dried to give the title product as a white solid which is identified by NMR spectral analysis.

Workup

  1. stirringstirred at room temperature for two hours
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. washThe solid is washed with water
  5. customair-dried

Sources & evidence

ORD record
ord-27ba8d73f9384dd8b20c6fd96055a60b
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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