Ethyl Acetate → 4-Acetamido-N-(2-amino-5-(thiazol-2-yl)phenyl)benzamide

HRID 252843

Reaction equation

HRID 252843 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:12])=[CH:10][CH:11]=1.[C:14]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].CCOC(C)=O>C(#N)C.N1C=CC=CC=1>[C:14]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:13][C:8]2[CH:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH:11]=[CH:10][C:9]=2[NH2:12])=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 70103414-Acetamidobenzoyl chlorideHCID 130078124-(Thiazol-2-yl)benzene-1,2-diamine

Product 1

HCID 597366844-Acetamido-N-(2-amino-5-(thiazol-2-yl)phenyl)benzamideYield 5.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of 222a (47 mg, 0.25 mmol) in acetonitrile (10 mL) and pyridine (20 uL) was added 4-acetamidobenzoyl chloride (49 mg, 0.25 mmol) in acetonitrile (1 mL) at 0° C. for 15 min. The reaction mixture was warmed up to room temperature and stirred for 4 hours, concentrated under reduced pressure. The crude was diluted in DCM and washed with NaHCO3 and brine. The organic layer was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3), then EtOAc (100%) to afford the title compounds 223 (3 mg, 4% yield) and 224a (5 mg, 5% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe crude was diluted in DCM
  3. washwashed with NaHCO3 and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3)

Sources & evidence

ORD record
ord-40fc5002ce4e4f40b706f1dcde50eab1
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Linked notes

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