Dimethylformamide → HCID 13532322, compound

HRID 979402Notes

Reaction equation

HRID 979402 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[N+:13]([O-:14])=[C:12]3[CH2:15][CH2:16][CH2:17][CH2:18][C:11]3=[N:10]2)=[C:4]([F:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:31](Br)[C:32]#[CH:33]>O>[Cl:1][C:2]1[C:7]([O:8][CH2:33][C:32]#[CH:31])=[CH:6][C:5]([N:9]2[N+:13]([O-:14])=[C:12]3[CH2:15][CH2:16][CH2:17][CH2:18][C:11]3=[N:10]2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 13532320HCID 13532320, compound

Product 1

HCID 13532322HCID 13532322, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-1,2,3-benzotriazol-1-oxide (1 g), potassium carbonate (0.3 g) and dimethylformamide (5 ml), propargyl bromide (0.6 g) was added, and the resultant mixture was stirred at 70° to 80° C. for 4 hours. After cooling, water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of n-hexane and ethyl acetate as a developing solvent to give 0.15 g of 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5,6,7-tetrahydro-1,2,3-benzotriazol-1-oxide (Compound No. 12). M.P., 155°-156° C.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel thin layer chromatography
  8. additiona mixture of n-hexane and ethyl acetate as a developing solvent

Sources & evidence

ORD record
ord-1089fe04bf5248b19c9b2217fc5a38bf
Source dataset
uspto-grants-1987_05
Patent number
US04668278

Reaction notes

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