3-Aminobenzoic Acid → HCID 11448255, compound

HRID 352379Notes

Reaction equation

HRID 352379 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13].O1CCCC1>[OH-].[Na+]>[C:15]1([O:14][C:12]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 74193-Aminobenzoic AcidHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformate

Product 1

HCID 11448255HCID 11448255, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

After 274.3 g of 3-aminobenzoic acid was dissolved in 4L of a 0.5N aqueous solution of sodium hydroxide, a solution of 328.8 g of phenyl chloroformate in 1L of tetrahydrofuran was added dropwise at 10° C. The reaction mixture was stirred at the same temperature for 1 hour, and then at room temperature for 1 hour. Crystals so precipitated were collected by filtration with suction, washed with water, dried and then recrystallized from ethanol to obtain 412 g of the title compound.

Workup

  1. waitat room temperature for 1 hour
  2. customCrystals so precipitated
  3. filtrationwere collected by filtration with suction
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e35c491c768a4ceb85ee3fce773e9aa8
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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