Phosphorus oxychloride → HCID 86660655, compound

HRID 1619313Notes

Reaction equation

HRID 1619313 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:22][CH:23]2[CH2:28][CH2:27][C:26](=O)[NH:25][CH2:24]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:22][CH:23]2[CH2:24][N:25]3[C:26](=[N:1][C:2]4[C:3]([C:4]3=[O:6])=[CH:7][CH:8]=[C:9]([Br:11])[CH:10]=4)[CH2:27][CH2:28]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 886912-Amino-4-bromobenzoic acidHCID 86660656HCID 86660656, compound

Product 1

HCID 86660655HCID 86660655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-4-bromobenzoic acid (1.4 g, 6.6 mmol, 1.1 equiv), 6-oxopiperidin-3-yl 4-bromobenzenesulfonate (2 g, 6.0 mmol, 1 equiv), and phosphoryl trichloride (4 mL) in 1,4-dioxane (100 mL) was stirred at 80° C. for two hours. After it was cooled to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e9746cf89f5d41d9988516ff50f84560
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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