p-Toluenesulfonic acid → HCID 46840738, compound

HRID 1846281Notes

Reaction equation

HRID 1846281 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[CH3:14].[NH2:15][C:16]1[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=1)=[O:19].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([C:9]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=3)[C:18](=[O:19])[C:17]3[C:16](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:15]=2)=[CH:7][C:6]=1[CH3:14]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 23665763Sodium BisulfiteHCID 28267823HCID 28267823, compoundHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

Product 1

HCID 46840738HCID 46840738, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
155 °C

Procedure

To a mixture of 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.570 g, 2.96 mmol) and 2-amino-N-(4-iodo-phenyl)-benzamide (1.00 g, 2.96 mmol) in N,N-dimethylacetamide (10 mL) was added sodium hydrogen sulfite (0.470 g, 4.44 mmol) and p-toluenesulfonic acid (0.280 g, 1.48 mmol). The reaction mixture was heated at 155° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with cold water (20 mL) to produce the precipitate. The yellow solid was filtered, washed with cold water (2×20 mL), methanol and dried under vacuum to provide crude product, which was purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent) to give the title compound as white solid. Yield: 0.20 g (13%). MP 101-103° C. 1H-NMR (400 MHz, CDCl3): δ 8.38 (d, 1H), 7.81-7.78 (m, 2H), 7.75 (d, 2H), 7.59-7.48 (m, 1H), 7.01-6.85 (m, 4H), 3.98-3.81 (m, 4H), 2.40 (s, 6H), 2.01 (t, 1H). MS (ES+) m/z: 513.09 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto produce the precipitate
  3. filtrationThe yellow solid was filtered
  4. washwashed with cold water (2×20 mL), methanol
  5. customdried under vacuum
  6. customto provide crude product, which
  7. customwas purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-9c24f72869ba4789b9d188878314583d
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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