Anthranilic Acid → 2-amino-N-(4-tert-butylphenyl)benzamide

HRID 969687Notes

Reaction equation

HRID 969687 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)=[O:16]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 3351772-amino-N-(4-tert-butylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-tert-butyl-phenylamine (5.8 mL, 36.5 mmol), 2-amino-benzoic acid (5.0 g, 36.5 mmol), TBTU (12.9 g, 40.2 mmol) and DIEA (6.7 mL, 40.2 mmol) in 5 mL of DMF was heated (50° C.) for 12 h in a sealed tube. The mixture was diluted with EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, 20% EtOAc/hexane) and crystallized from EtOH:H2O (3:1) to afford a yellow solid. MS (ES+): 269.4. (M+H)+. Calc'd for C17H20N2O-268.35.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (SiO2, 20% EtOAc/hexane)
  6. customcrystallized from EtOH:H2O (3:1)
  7. customto afford a yellow solid

Sources & evidence

ORD record
ord-e6b994e230c646c7b02fd7b05b3621ba
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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