Triethylamine → 4-amino-N-(4-tert-butylphenyl)-3-nitrobenzamide

HRID 1515030Notes

Reaction equation

HRID 1515030 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36].C(N(CC)CC)C.[C:45]([C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1)([CH3:48])([CH3:47])[CH3:46]>C(OCC)(=O)C.CN(C=O)C>[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:53][C:52]2[CH:54]=[CH:55][C:49]([C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:50][CH:51]=2)=[O:32])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 698614-Tert-ButylanilineHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 87798564-amino-N-(4-tert-butylphenyl)-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To DMF (10 mL) was added HATU (3.61 g, 9.50 mmol), 4-amino-3-nitrobenzoic acid (1.15 g, 6.32 mmol), triethylamine (1.32 mL, 958 mg, 9.47 mmol), and 4-tert-butylaniline (1.0 mL, 945 mg, 6.33 mmol). The mixture was stirred at ambient temperature for 18 h then was poured into ethyl acetate and extracted once with water and five times with brine. The organic phase was dried, filtered, and the solvent removed under reduced pressure. The residue was purified by chromatography using gradient of a 30-70% heptane/ethyl acetate to afford 4-amino-N-(4-tert-butylphenyl)-3-nitrobenzamide. MS (ESI) m/z 314.1 (M+H); retention time 1.50 min (Method 10), which was used directly in the next step.

Workup

  1. extractionextracted once with water and five times with brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c9f2f7d2bb954d6a926985781ebeb092
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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