Thionyl Chloride → 2-Amino-6-methyl-N-phenylbenzamide

HRID 1746297Notes

Reaction equation

HRID 1746297 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([OH:10])=O>C1C=CC=CC=1>[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:7]=1)=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1512106-Methylanthranilic acid

Product 1

HCID 167877862-Amino-6-methyl-N-phenylbenzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (14.5 mL, 198 mmol) was added to a solution of 2-amino-6-methylbenzoic acid (10.0 g, 66.1 mmol) in benzene (250 mL). The resulting suspension was heated to reflux and stirred overnight. After cooling, the reaction was concentrated in vacuo, and the resulting residue was dissolved in chloroform (300 mL). Aniline (15, mL, 165 mmol) was added, and the mixture heated to reflux. After three hours, the reaction was allowed to cool and the resulting suspension was filtered. The filtrate was subjected to flash chromatography, and the Crude product recrystallized from isopropanol to provide compound 15 as a yellow crystalline solid. MS (ES): m/z 227 (M+H), 134. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.75 (d, 2H, J=7.9 Hz), 7.32 (t, 2H, J=7.8 Hz), 7.07 (t, 1H, J=7.3 Hz), 7.00 (t, 1H, J=7.8 Hz), 6.58 (d, 1H, J=8.1 Hz); 6.46 (d, 1H, J=7.4 Hz), 4.98 (br. s, 2H), 2.21 (s, 3H). The reaction described above and compound 15 are shown below.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. concentrationthe reaction was concentrated in vacuo
  5. dissolutionthe resulting residue was dissolved in chloroform (300 mL)
  6. additionAniline (15, mL, 165 mmol) was added
  7. temperaturethe mixture heated to reflux
  8. waitAfter three hours
  9. temperatureto cool
  10. filtrationthe resulting suspension was filtered
  11. customthe Crude product recrystallized from isopropanol

Sources & evidence

ORD record
ord-5ef3b6984162415e96be30ac4284dee5
Source dataset
uspto-grants-2015_10
Patent number
US09149477B2

Reaction notes

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