Triethylamine → HCID 11816733, compound

HRID 1368016Notes

Reaction equation

HRID 1368016 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].[C:11](Cl)(=O)[CH2:12][CH3:13].C([N:18](CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=C(C)C=1>[NH2:18][C:7]1[C:2]2[N:1]=[C:11]([CH2:12][CH3:13])[O:10][C:3]=2[C:4]([Cl:9])=[CH:5][C:6]=1[F:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11275173HCID 11275173, compound

Product 1

HCID 11816733HCID 11816733, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

2-Amino-6-chloro-4-fluorophenol (3 g) was dissolved in m-xylene (150 ml) containing propionyl chloride (2.05 g), triethylamine (2.24 g) and pyridinium p-toluenesulfonate (2.8 g). The mixture was refluxed under N2 for 4 hours, then cooled to room temperature and passed through a silica gel column eluted with a mixture of hexane and ether (5:1) to yield the title compound as a pale-brown solid (2.85 g). 1H-NMR (CDCl3, 300 MHz): 1.45(3H, t, J=7.6 Hz), 2.98(2H, q, J=7.6 Hz), 7.07(1 H, dd, J=2.3 Hz, 9.2 Hz), 7.27(1 H, dd, J=2.4 Hz, 8.1 Hz) ppm.

Workup

  1. temperatureThe mixture was refluxed under N2 for 4 hours
  2. washeluted with a mixture of hexane and ether (5:1)

Sources & evidence

ORD record
ord-fb4c507852da4b2e9e597a0702a8a22b
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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