Acetic Acid → HCID 12920002, compound

HRID 354805Notes

Reaction equation

HRID 354805 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]([NH2:15])=[C:8]([O:16][CH3:17])[C:7]=1[O:18][CH3:19].[O-:20][C:21]#[N:22].[K+].[OH-].[Na+]>O>[Cl:5][C:6]1[CH:14]=[C:10]2[C:9](=[C:8]([O:16][CH3:17])[C:7]=1[O:18][CH3:19])[NH:15][C:21](=[O:20])[NH:22][C:11]2=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11378442Potassium cyanateHCID 12920000HCID 12920000, compound

Product 1

HCID 12920002HCID 12920002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Acetic acid (10.5 g., 0.175 mole) was added to a vigorously stirred suspension of 5-chloro-3,4-dimethoxyanthranilic acid (28.9 g., 0.125 mole) in 600 ml. water. Then 506 ml. 5% potassium cyanate (0.312 mole) solution was gradually added and stirred 1 hour at 40° C. After cooling the reaction mixture to 20° C., 175 g. (4.37 moles) of sodium hydroxide pellets were added while maintaining the temperature below 40° C. The reaction mixture was heated to 90° C. for 45 minutes. Upon cooling in an ice bath, the sodium salt of the product precipitated, was filtered, resuspended in 125 ml. water, acidified with concentrated hydrochloric acid, cooled and filtered to yield 25.8 g. (80%) of colorless, pure product, M.P. 272°-3° C.

Workup

  1. temperatureAfter cooling the reaction mixture to 20° C.
  2. temperaturewhile maintaining the temperature below 40° C
  3. temperatureThe reaction mixture was heated to 90° C. for 45 minutes
  4. temperatureUpon cooling in an ice bath
  5. customthe sodium salt of the product precipitated
  6. filtrationwas filtered
  7. temperaturecooled
  8. filtrationfiltered
  9. customto yield 25.8 g

Sources & evidence

ORD record
ord-8b3b4ece1d2a4470aa41288d5125450b
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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