Water → 3-[6-chloro-3-(2-propenyl)-2(3H)-benzothiazolon-5-yl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

HRID 621365Notes

Reaction equation

HRID 621365 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]([N:14]2[N:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[O:16][C:15]2=[O:23])=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1.[CH2:24](Br)[C:25]#[CH:26].O>CN(C)C=O>[Cl:3][C:4]1[C:13]([N:14]2[N:18]=[C:17]([C:19]([CH3:20])([CH3:22])[CH3:21])[O:16][C:15]2=[O:23])=[CH:12][C:7]2[N:8]([CH2:26][CH:25]=[CH2:24])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 142806403-[6-chloro-2(3H)-benzothiazolon-5-yl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 142806503-[6-chloro-3-(2-propenyl)-2(3H)-benzothiazolon-5-yl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-oneYield 24.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A dispersion of sodium hydride (50% oil; 0.16 g) in dry N,N-dimethylformamide (3 ml) was cooled to 0° C., and a solution of 3-[6-chloro-2(3H)-benzothiazolon-5-yl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (1.00 g) in dry N,N-dimethylformamide (3 ml) was dropwise added thereto at the same temperature, followed by stirring at the same temperature for 30 minutes. Upon addition of propargyl bromide (0.44 g), the resultant mixture was heated to 50° C. and stirred for 5 hours. The reaction mixture was allowed to cool, combined with water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography with a mixture of ether and hexane (1:1) as an eluent to give 3-[6-chloro-3-(2-propenyl)-2(3H)-benzothiazolon-5-yl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one (0.28 g). nD25.5 1.5703.

Workup

  1. stirringstirred for 5 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel thin layer chromatography with a mixture of ether and hexane (1:1) as an eluent

Sources & evidence

ORD record
ord-55d3b901cda1486ab2b6e8181b6ef1ee
Source dataset
uspto-grants-1989_04
Patent number
US04824465

Reaction notes

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