Acetic Acid → Methyl 2-[p-(6-acetamido-5-fluoro-1H-benzotriazol-1-yl)phenoxy]propionate

HRID 1078009Notes

Reaction equation

HRID 1078009 reaction equation
[C:1]([NH:4][C:5]1[C:6]([F:26])=[CH:7][C:8]([NH2:25])=[C:9]([CH:24]=1)[NH:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2].C(O)(=O)C.[N:31]([O-])=O.[Na+]>O1CCCC1.O>[C:1]([NH:4][C:5]1[C:6]([F:26])=[CH:7][C:8]2[N:25]=[N:31][N:10]([C:11]3[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=3)[C:9]=2[CH:24]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 19430913Methyl 2-[p-(5-acetamido-2-amino-4-fluoroanilino)phenoxy]propionateHCID 23668193Sodium Nitrite

Product 1

HCID 19430917Methyl 2-[p-(6-acetamido-5-fluoro-1H-benzotriazol-1-yl)phenoxy]propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-[p-(5-acetamido-2-amino-4-fluoroanilino)phenoxy]propionate (7 g, 0.019 mol) in tetrahydrofuran is added dropwise to a 50% acetic acid solution at 0° C. To the resultant mixture, a solution of sodium nitrite (2.81 g, 0.041 mol) in water is added dropwise. After the addition is complete, the reaction mixture is warmed to room temperature, stirred for 3 days and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with brine and water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as an orange solid which is identified by NMR spectral analyses.

Workup

  1. additionAfter the addition
  2. extractionThe aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with brine and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ef21f97bbe64451a9e2fea48f3a64c8
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

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