Hydrochloric Acid → HCID 10731836, compound

HRID 411276Notes

Reaction equation

HRID 411276 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(=O)([O-])O.[Na+].Cl>O.CCOCC>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformate2×HCID 755984-Amino-3-methylbenzoic acidHCID 516892Sodium Bicarbonate2×

Product 1

HCID 10731836HCID 10731836, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

4-Amino-3-methylbenzoic acid (5.0 g) was suspended in water (80 ml) and, thereafter, an ether solution (20 ml) of carbobenzoxychloride (3.7 g) and sodium hydrogen carbonate (3.6 g) were alternately added to the suspension under cooling with ice. Following stirring for 2.5 h at room temperature, an ether solution (95 ml) of carbobenzoxychloride (3.7 g) and sodium hydrogen carbonate (7.2 g) were further added alternately under cooling with ice, and the mixture was stirred for 1.5 h at room temperature. After rendering the reaction solution acidic with 4N HCl, the separating insoluble matter was recovered by filtration. The recovered solids were vacuum-dried to yield the end product (2.8 g).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 1.5 h at room temperature
  4. filtrationthe separating insoluble matter was recovered by filtration
  5. customThe recovered solids were vacuum-dried

Sources & evidence

ORD record
ord-268c5376447041578de4ead93e8b68b7
Source dataset
uspto-grants-2003_05
Patent number
US06559149B1

Reaction notes

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