Acetic Acid → N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]acetamide

HRID 259744Notes

Reaction equation

HRID 259744 reaction equation
[NH2:1][C:2]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[C:4]([F:21])[CH:3]=1.C(O)(=O)C.[N:26]([O-])=O.[Na+].C(Cl)Cl.C(OCC)(=O)C>O1CCCC1.O>[F:21][C:4]1[C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:10][C:11]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:26]=[N:1][C:2]=2[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 153460654'-Amino-2'-fluoro-5'-(o-methoxyanilino)acetanilideHCID 21226138Dichloromethane ethylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 15346066N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4'-amino-2'-fluoro-5'-(o-methoxyanilino)acetanilide (11.0 g, 0.038 mol) in tetrahydrofuran is added dropwise to a 50% acetic acid solution at 0° C. To the resultant mixture, a solution of sodium nitrite (5.51 g, 0.080 mol) in water is added dropwise. After the addition is complete, the reaction mixture is stirred at room temperature for 2 hours and filtered to obtain a solid. The filtrate is extracted with ethyl acetate and the organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark solid. Flash column chromatography of the combined solids using silica gel and a (3:1) methylene chloride/ethyl acetate solution gives the title product as a greenish-brown solid, mp 174°-175° C.

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. customto obtain a solid
  4. extractionThe filtrate is extracted with ethyl acetate
  5. washwashed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a dark solid

Sources & evidence

ORD record
ord-26b75cdd16dc404fa4263484c252708a
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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