Hydrochloric Acid → HCID 67344183, compound

HRID 1673535Notes

Reaction equation

HRID 1673535 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[NH2:18][C:19]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].Cl>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:18][C:19]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[O:8])#[N:2]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 158753-Cyanobenzoic acidHCID 65578Oxalyl chlorideHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67344183HCID 67344183, compound

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 0.17 g of 3-cyanobenzoic acid were added 2.5 mL of methylene chloride, 0.015 mL of N,N-dimethylformamide and 0.095 mL of oxalyl chloride at room temperature sequentially and stirred at the same temperature for 30 minutes. The reaction mixture was added to a mixed solution of 3.0 mL of methylene chloride and 0.35 mL of triethylamine containing 0.26 g of tert-butyl 2-amino-4-phenoxybenzoate at room temperature and stirred at the same temperature for 10 minutes. Ethyl acetate, 1.0 mol/L hydrochloric acid and tetrahydrofuran were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform] to obtain 0.20 g of tert-butyl 2-(3-cyanobenzamido)-4-phenoxybenzoate as white solid.

Workup

  1. stirringstirred at the same temperature for 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform]

Sources & evidence

ORD record
ord-2198e85dc7754ead8eec83327540eea3
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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