Water → HCID 68525769, compound

HRID 884141Notes

Reaction equation

HRID 884141 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:43])[O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>C1COCC1>[C:37]1([O:36][C:35](=[O:43])[NH:3][C:4]2[CH:27]=[CH:26][C:7]([O:8][C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:25])[C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=4)=[CH:13][N:14]=3)=[CH:6][CH:5]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 68526231HCID 68526231, compound

Product 1

HCID 68525769HCID 68525769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-[6-(4-aminophenoxy)pyridin-3-yl]-3,4-dichlorobenzamide dihydrochloride (700 mg, 1.57 mmol) in THF (20 mL) was added triethylamine (1.1 mL, 7.89 mmol). To the resulting solution was then added dropwise phenyl chlorocarbonate (0.39 mL, 3.14 mmol) under ice cooling. The resulting reaction solution was stirred for 1 hour at room temperature. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated, whereupon the residue solidified into a powder. The powder was filtered, and washed with diethyl ether, to thereby yield 470 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. customevaporated, whereupon the residue
  6. filtrationThe powder was filtered
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-bc2809346df94b8b8555d89be7e58d99
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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