Hydrochloric Acid → HCID 67175348, compound

HRID 2383994Notes

Reaction equation

HRID 2383994 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[OH:26].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH2:10][O:26][C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[Cl:18])[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 67175327HCID 67175327, compound

Product 1

HCID 67175348HCID 67175348, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-bromomethyl-2-propionylamino-benzoic acid methyl ester (200 mg, 0.67 mmol), 2,4-dichloro-phenol (119 mg, 0.73 mmol) and potassium carbonate (278 mg, 2.01 mmol) in acetone (5 ml) was heated to reflux. After 4 hours, the reaction mixture was allowed to reach room temperature, was acidified with 1 M HCl and the resulting precipitate collected by filtration, washed with water and dried under vacuum to give pure 5-(2,4-dichloro-phenoxymethyl)-2-propionylamino-benzoic acid methyl ester (184 mg, 72%). This was hydrolyzed in ethanol (3 mL) and 1.0 M NaOH (3 mL) overnight and then acidified with 1.0 M HCl. The resulting precipitate was collected by filtration, washed with water and dried under vacuum (165 mg, 93%). 1H-NMR (DMSO-d6) δ 1.12 (t, 3H), 2.42 (q, 2H), 5.21 (s, 2H), 7.27 (d, 1H), 7.39 (dd, 1H), 7.60 (d, 1H), 7.66 (dd, 1H), 8.09 (d, 1H), 8.53 (d, 1H), 11.18 (s, 1H), 13.71 (bs, 1H).

Workup

  1. temperaturewas heated to reflux
  2. customto reach room temperature
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e5de6c6343524ec8895cb9b3d54f77e6
Source dataset
uspto-grants-2012_09
Patent number
US08263658B2

Reaction notes

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