Hydrochloric Acid → HCID 23123812, compound

HRID 511755Notes

Reaction equation

HRID 511755 reaction equation
[OH-].[Na+].Cl[C:4]([O:6][CH2:7][C:8]([Cl:11])([Cl:10])[Cl:9])=[O:5].Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18]>>[Cl:9][C:8]([Cl:11])([Cl:10])[CH2:7][O:6][C:4]([NH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])=[O:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 14798Sodium Hydroxide2×HCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 23123812HCID 23123812, compoundYield 87%

Procedure

To an aqueous solution (200 ml) of 8.22 g of m-aminobenzoic acid and 4.8 g of sodium hydroxide was dropwise added 25.0 g of 2,2,2-trichloroethyl chloroformate at room temperature. During the dropwise addition, the reaction solution was controlled to pH 10 or more by appropriately adding a 1N sodium hydroxide aqueous solution. After the reaction, the solution was controlled to pH 1 by adding 1N hydrochloric acid, and the precipitates were collected by filtration. The resultant crude crystals were dried and then washed with a ethyl acetate/n-hexane mixed solvent to obtain 16.2 g (yield 87%) of the title compound as a solid.

Workup

  1. customat room temperature
  2. additionDuring the dropwise addition
  3. customAfter the reaction
  4. filtrationthe precipitates were collected by filtration
  5. customThe resultant crude crystals were dried
  6. washwashed with a ethyl acetate/n-hexane mixed solvent

Sources & evidence

ORD record
ord-8a1a98efe5034bc480f9e9feed445d38
Source dataset
uspto-grants-2015_08
Patent number
US09101135B2

Reaction notes

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