Water → 2-[3(2-propynyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-4, 5, 6,7-tetrahydro-2H-benzotriazole-1-oxide

HRID 1089879Notes

Reaction equation

HRID 1089879 reaction equation
[H-].[Na+].[F:3][C:4]1[C:13]([N:14]2[N+:18]([O-:19])=[C:17]3[CH2:20][CH2:21][CH2:22][CH2:23][C:16]3=[N:15]2)=[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>[CH2:26]([N:8]1[C:7]2[CH:12]=[C:13]([N:14]3[N+:18]([O-:19])=[C:17]4[CH2:20][CH2:21][CH2:22][CH2:23][C:16]4=[N:15]3)[C:4]([F:3])=[CH:5][C:6]=2[S:10][C:9]1=[O:11])[C:25]#[CH:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 143288132-[6fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide

Product 1

HCID 143288162-[3(2-propynyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-4, 5, 6,7-tetrahydro-2H-benzotriazole-1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dispersion of sodium hydride (60% oil; 31 mg) in dry N,N-dimethylformamide (3 ml) was added 2-[6-fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide (220 mg) at 0° C., and the resultant mixture was stirred at the same temperature for 30 minutes, followed by addition of propargyl bromide (94 mg). The mixture was allowed to react at 50° to 60° C. for 3 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and toluene (1:9) as an eluent to give 2-[3-(2-propynyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide (Compound No. 5; 120 mg). nD25.4 1.5988.

Workup

  1. customto react at 50° to 60° C. for 3 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel thin layer chromatography
  7. additiona mixture of ethyl acetate and toluene (1:9) as an eluent

Sources & evidence

ORD record
ord-8d263eae319b487ba75d3f027d5f271f
Source dataset
uspto-grants-1992_01
Patent number
US05079368

Reaction notes

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