Chloroacetic Acid → HCID 86606908, compound

HRID 2116772Notes

Reaction equation

HRID 2116772 reaction equation
[N:1]1([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]#[N:17])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([OH:31])=[O:30].Cl>[Cl-].C[N+](C)(C)C.CC(C)=O.O>[N:1]1([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:28][C:29]([OH:31])=[O:30])=[C:11]([C:16]#[N:17])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 300Chloroacetic Acid3×HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium Carbonate3×HCID 86606906HCID 86606906, compound

Product 1

HCID 86606908HCID 86606908, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 6379Tetramethylammonium chlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
30 °C

Procedure

3-Cyano-4-hydroxybenzoic acid (4-morpholinyl)amide (10 g, 43.1 mmol), sodium iodide (3.2 g, 21.3 mmol), potassium carbonate (17.9 g, 129 mmol) and tetramethylammonium chloride (0.47 g, 4.29 mmol) are suspended in acetone (125 mL) and water (15 mL), and the mixture is refluxed for 1 hour. After cooling to 30° C., chloroacetic acid (8.1 g, 86.2 mmol) is added. The mixture is refluxed for 5 hours, cooled to 30° C., and thereto are added potassium carbonate (11.9 g, 86.2 mmol) and chloroacetic acid (8.1 g, 86.2 mmol) successively. The mixture is refluxed for 3 hours, cooled to 30° C., and thereto are added potassium carbonate (11.9 g, 86.2 mmol) and chloroacetic acid (8.1 g, 86.2 mmol) successively. The mixture is refluxed for 3 hours, and thereto is added water (140 mL, 14 V), followed by addition of conc. hydrochloric acid (35 mL, 0.40 mol) at 40° C. or below. The mixture is stirred at 20° C. for one hour. The precipitated crystals are collected by filtration, and dried with a conical dryer to give 3-cyano-4-carboxymethoxybenzoic acid (4-morpholinyl)amide (11.6 g, 93.0%, content: 96.6%). Mp: 205-206° C.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperaturecooled to 30° C.
  3. temperatureThe mixture is refluxed for 3 hours
  4. temperaturecooled to 30° C.
  5. temperatureThe mixture is refluxed for 3 hours
  6. filtrationThe precipitated crystals are collected by filtration
  7. customdried with a conical dryer

Sources & evidence

ORD record
ord-34210d1659f14c01a4ddd198d5a1e9a6
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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